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11.0133 0 TD
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[(\(E\) Co)-7.5(mp)5.9(lex)-7.5( )]TJ
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5.3733 0 TD
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/TT4 1 Tf
0.4933 0 TD
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[(o)-11.6(f)-5.2( al)-7.1(kyn)-11.6(es.)]TJ
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0 Tw
(13)Tj
9 0 0 9 55.0403 453.48 Tm
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(2a)Tj
ET
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49.4 516.24 496.56 -0.36 re
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1 1 1 sc
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BT
/TT8 1 Tf
7.0003 0 0 7.0003 305.6367 746.8207 Tm
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0 Tc
(R)Tj
ET
1 i
324.137 759.071 m
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f
BT
7.0003 0 0 7.0003 337.438 746.8207 Tm
(H)Tj
ET
336.588 751.871 m
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f
BT
7.0003 0 0 7.0003 321.3874 774.2719 Tm
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ET
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f
BT
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(OR')Tj
ET
377.39 752.321 m
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f
BT
7.0003 0 0 7.0003 361.889 774.9218 Tm
(O)Tj
ET
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f
BT
7.0003 0 0 7.0003 466.3932 745.5207 Tm
(R)Tj
ET
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f
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f
BT
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(OR')Tj
ET
529.346 750.371 m
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f
BT
7.0003 0 0 7.0003 482.1938 772.9218 Tm
(OAc)Tj
ET
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f
BT
7.0003 0 0 7.0003 513.8451 772.9218 Tm
(O)Tj
ET
515.145 771.722 0.6 -14.951 re
f
517.345 771.722 0.6 -14.951 re
f
BT
7.0003 0 0 7.0003 344.0383 760.0712 Tm
(+)Tj
7.3714 2.2571 TD
(1\) LDA/THF)Tj
0 -1.2786 TD
(2\) sat. NH)Tj
5.2502 0 0 5.2502 427.1484 765.609 Tm
(4)Tj
7.0003 0 0 7.0003 430.0683 766.9215 Tm
(Cl \(2 equiv\))Tj
-4.9252 -2.0786 TD
(3\) Lipase \(PS-C\))Tj
0 -1.2786 TD
(4\) Cat. )Tj
/TT10 1 Tf
3.2787 -0.0002 TD
(1)Tj
/TT8 1 Tf
0.5562 0.0002 TD
(, 6 mol%)Tj
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(5\) )Tj
/TT12 1 Tf
1.1669 -0.0002 TD
(p)Tj
/TT8 1 Tf
0.5562 0.0002 TD
(-ClC)Tj
5.2502 0 0 5.2502 421.65 733.1577 Tm
(6)Tj
7.0003 0 0 7.0003 424.5699 734.4703 Tm
(H)Tj
5.2502 0 0 5.2502 429.6252 733.1577 Tm
(4)Tj
7.0003 0 0 7.0003 432.5452 734.4703 Tm
(OAc)Tj
-5.2791 -1.2786 TD
( TBME, 60 C, 6 d)Tj
ET
/Cs5 CS 0.161 0.145 0.149 SC
0 J 0 j 0.48 w 4 M []0 d
467.242 761.221 m
390.94 761.221 l
S
472.493 761.221 m
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466.997 762.301 467.242 761.775 467.242 761.221 c
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f
1 1 1 sc
303.92 702.84 229.92 -72.96 re
f
0.161 0.145 0.149 sc
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f
335.788 641.535 m
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f
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f
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f
335.788 667.736 m
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f
324.438 661.186 m
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f
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f
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f
370.439 648.085 m
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f
370.439 661.186 m
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f
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f
347.738 661.186 m
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f
382.09 668.236 m
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f
382.09 681.337 m
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f
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f
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f
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f
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f
402.74 674.786 m
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f
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403.541 674.786 l
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f
382.74 681.337 m
382.44 681.537 l
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394.94 685.937 l
395.24 685.687 l
395.09 685.337 l
f
BT
7.0003 0 0 7.0003 304.6867 638.4349 Tm
(HO)Tj
ET
315.987 641.835 m
314.787 643.885 l
323.787 648.085 l
324.137 647.885 l
324.137 647.485 l
f
346.238 674.786 m
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f
382.64 695.037 m
384.99 694.787 l
382.84 681.987 l
382.44 681.537 l
382.14 682.087 l
f
BT
7.0003 0 0 7.0003 396.6902 695.7872 Tm
(R)Tj
5.2502 0 0 5.2502 401.7456 698.4122 Tm
(1)Tj
ET
396.94 694.837 m
399.19 694.087 l
395.59 685.737 l
395.24 685.687 l
394.94 685.937 l
f
BT
7.0003 0 0 7.0003 405.8406 685.0868 Tm
(R)Tj
5.2502 0 0 5.2502 410.896 687.7119 Tm
(2)Tj
ET
404.841 688.437 m
405.241 686.087 l
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f
402.49 687.787 m
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f
400.14 687.137 m
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399.49 686.987 l
f
397.74 686.487 m
397.89 685.737 l
397.24 685.687 l
397.14 686.337 l
f
BT
7.0003 0 0 7.0003 318.9373 649.0853 Tm
(3)Tj
2.15 -1.9286 TD
(4)Tj
1.5857 0.3429 TD
(5)Tj
1.9214 -0.5643 TD
(6)Tj
ET
444.142 642.685 m
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f
455.492 636.135 m
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f
466.843 642.685 m
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455.492 635.385 l
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f
464.543 644.135 m
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f
466.843 655.786 m
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467.443 642.685 l
467.143 642.485 l
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f
455.492 662.336 m
455.492 663.036 l
466.793 656.536 l
467.143 655.936 l
466.843 655.786 l
f
444.142 655.786 m
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443.492 656.136 l
455.492 663.036 l
455.492 662.336 l
f
478.793 636.135 m
478.793 635.385 l
467.143 642.135 l
467.143 642.485 l
467.443 642.685 l
f
490.144 642.685 m
490.494 642.485 l
490.794 642.285 l
478.793 635.385 l
478.793 636.135 l
f
490.144 655.786 m
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490.794 655.786 l
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f
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f
467.443 655.786 m
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467.493 656.536 l
478.493 662.836 l
478.793 662.686 l
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f
501.794 662.836 m
502.144 662.686 l
502.144 662.336 l
490.794 655.786 l
490.494 655.936 l
490.494 656.336 l
f
501.794 675.936 m
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501.794 662.836 l
f
490.494 682.487 m
490.494 683.237 l
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502.144 676.136 l
501.794 675.936 l
f
479.143 675.936 m
478.793 676.136 l
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490.494 683.237 l
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f
479.143 662.836 m
478.793 662.686 l
478.493 662.836 l
478.493 676.336 l
478.793 676.136 l
479.143 675.936 l
f
514.795 658.886 m
514.945 658.536 l
515.045 658.136 l
502.144 662.336 l
502.144 662.686 l
502.444 662.886 l
f
522.445 669.386 m
523.245 669.386 l
515.045 658.136 l
514.945 658.536 l
514.795 658.886 l
f
514.795 679.937 m
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515.295 680.337 l
523.245 669.386 l
522.445 669.386 l
f
502.444 675.936 m
502.144 676.136 l
502.544 676.586 l
514.645 680.537 l
514.945 680.287 l
514.795 679.937 l
f
465.943 669.386 m
468.343 669.386 l
467.493 656.536 l
467.143 655.936 l
466.793 656.536 l
f
502.344 689.637 m
504.744 689.387 l
502.544 676.586 l
502.144 676.136 l
501.844 676.686 l
f
BT
7.0003 0 0 7.0003 516.3948 690.387 Tm
(R)Tj
5.2502 0 0 5.2502 521.4502 693.0121 Tm
(1)Tj
ET
516.645 689.437 m
518.895 688.687 l
515.295 680.337 l
514.945 680.287 l
514.645 680.537 l
f
BT
7.0003 0 0 7.0003 525.5452 679.6865 Tm
(R)Tj
5.2502 0 0 5.2502 530.6005 682.3116 Tm
(2)Tj
ET
524.545 683.037 m
524.945 680.687 l
524.295 680.637 l
523.945 682.887 l
f
522.195 682.387 m
522.495 680.587 l
521.845 680.537 l
521.595 682.237 l
f
519.845 681.737 m
520.045 680.437 l
519.395 680.437 l
519.195 681.587 l
f
517.445 681.087 m
517.595 680.337 l
516.945 680.287 l
516.845 680.937 l
f
BT
7.0003 0 0 7.0003 431.5916 630.2346 Tm
(O)Tj
ET
437.792 634.285 m
437.342 634.735 l
444.692 642.085 l
445.142 641.635 l
f
436.092 635.985 m
435.642 636.435 l
443.592 644.435 l
444.042 643.985 l
f
BT
/TT10 1 Tf
7.0003 0 0 7.0003 413.7909 659.2858 Tm
(1)Tj
/TT8 1 Tf
-1.8213 -1.8427 TD
(acetone,)Tj
0.6643 -1.1214 TD
(56 C)Tj
ET
0.52 w
428.603 656.036 m
398.49 656.036 l
S
434.292 656.036 m
427.878 657.591 l
428.337 657.205 428.603 656.636 428.603 656.036 c
428.603 655.436 428.337 654.866 427.878 654.48 c
f
1 1 1 sc
303.92 613.2 226.92 -87.96 re
f
BT
7.0003 0 0 7.0003 304.1367 587.0491 Tm
0.161 0.145 0.149 sc
(R)Tj
ET
319.437 597.45 m
319.787 597.25 l
319.787 596.849 l
309.937 591.149 l
309.587 591.799 l
f
BT
7.0003 0 0 7.0003 330.1877 587.0491 Tm
(NH)Tj
ET
329.438 592.049 m
329.088 591.449 l
319.787 596.849 l
319.787 597.25 l
320.137 597.45 l
f
319.437 612.2 m
320.137 612.2 l
320.137 597.45 l
319.787 597.25 l
319.437 597.45 l
f
BT
7.0003 0 0 7.0003 349.9385 587.0491 Tm
(R')Tj
ET
340.888 590.099 8.45 -0.7 re
f
BT
7.0003 0 0 7.0003 483.0436 587.0491 Tm
(R)Tj
ET
498.344 597.45 m
498.694 597.25 l
498.694 596.849 l
488.894 591.149 l
488.544 591.799 l
f
BT
7.0003 0 0 7.0003 509.1447 587.0491 Tm
(N)Tj
ET
508.345 592.049 m
507.995 591.449 l
498.694 596.849 l
498.694 597.25 l
499.044 597.45 l
f
509.695 594.399 m
509.345 593.799 l
501.194 598.5 l
501.594 599.1 l
f
498.344 612.2 m
499.044 612.2 l
499.044 597.45 l
498.694 597.25 l
498.344 597.45 l
f
BT
7.0003 0 0 7.0003 523.9453 587.0491 Tm
(R')Tj
ET
514.795 590.099 8.55 -0.7 re
f
BT
7.0003 0 0 7.0003 405.6407 601.1997 Tm
(2 mol% )Tj
/TT10 1 Tf
3.6122 -0.0002 TD
(1)Tj
ET
411.641 559.698 m
410.941 559.298 l
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411.291 571.448 l
411.641 571.249 l
f
413.091 570.198 0.7 -9.45 re
f
421.641 553.898 m
421.641 553.098 l
410.941 559.298 l
411.641 559.698 l
f
431.692 559.698 m
432.392 559.298 l
421.641 553.098 l
421.641 553.898 l
f
431.692 571.249 m
432.042 571.448 l
432.392 571.249 l
432.392 559.298 l
431.692 559.698 l
f
429.542 570.198 0.7 -9.45 re
f
421.641 577.049 m
421.641 577.849 l
432.042 571.849 l
432.042 571.448 l
431.692 571.249 l
f
411.641 571.249 m
411.291 571.448 l
411.291 571.849 l
421.641 577.849 l
421.641 577.049 l
f
BT
/TT8 1 Tf
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(O)Tj
ET
420.241 585.549 0.7 -8.75 re
f
422.391 585.549 0.7 -8.75 re
f
BT
7.0003 0 0 7.0003 418.9412 538.7972 Tm
(O)Tj
ET
422.391 554.148 0.7 -9.05 re
f
420.241 554.148 0.7 -9.05 re
f
BT
7.0003 0 0 7.0003 439.642 574.6986 Tm
(OMe)Tj
ET
438.942 575.849 m
439.292 575.249 l
432.392 571.249 l
432.042 571.448 l
432.042 571.849 l
f
BT
7.0003 0 0 7.0003 388.44 574.6986 Tm
(MeO)Tj
ET
403.991 575.299 m
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411.291 571.849 l
411.291 571.448 l
410.941 571.249 l
f
0.56 w
462.017 595.899 m
374.839 595.899 l
S
468.143 595.899 m
461.236 597.574 l
461.731 597.159 462.017 596.546 462.017 595.899 c
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f
BT
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(Toluene, reflux)Tj
ET
1 1 1 sc
303.92 508.56 159 -33 re
f
0.161 0.145 0.149 sc
321.987 498.313 14.951 -0.7 re
f
321.987 495.613 14.951 -0.7 re
f
321.987 492.912 14.951 -0.7 re
f
BT
7.0003 0 0 7.0003 349.1878 492.5125 Tm
(R)Tj
ET
336.937 495.613 11.7 -0.7 re
f
BT
7.0003 0 0 7.0003 304.3361 492.5125 Tm
(R)Tj
ET
309.986 495.613 12 -0.7 re
f
448.892 495.613 m
449.042 495.263 l
448.892 494.913 l
434.191 494.913 l
434.041 495.263 l
434.191 495.613 l
f
435.191 498.313 12.701 -0.7 re
f
BT
7.0003 0 0 7.0003 420.9905 503.1129 Tm
(H)Tj
ET
426.391 502.463 m
426.891 502.963 l
434.191 495.613 l
434.041 495.263 l
433.591 495.263 l
f
BT
7.0003 0 0 7.0003 457.0919 503.1129 Tm
(H)Tj
ET
456.242 502.963 m
456.742 502.463 l
449.542 495.263 l
449.042 495.263 l
448.892 495.613 l
f
BT
7.0003 0 0 7.0003 456.9418 481.962 Tm
(R)Tj
ET
456.842 487.962 m
456.342 487.462 l
448.892 494.913 l
449.042 495.263 l
449.542 495.263 l
f
BT
7.0003 0 0 7.0003 420.7905 481.962 Tm
(R)Tj
ET
426.241 486.912 m
425.741 487.412 l
433.591 495.263 l
434.041 495.263 l
434.191 494.913 l
f
0.56 w
407.714 495.263 m
362.788 495.263 l
S
413.84 495.263 m
406.933 496.937 l
407.428 496.522 407.714 495.909 407.714 495.263 c
407.714 494.616 407.428 494.003 406.933 493.588 c
f
BT
/TT10 1 Tf
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(1)Tj
/TT8 1 Tf
-2.2571 -1.5141 TD
(H)Tj
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(2)Tj
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( \(500 psi\))Tj
-1.1393 -1.2786 TD
( THF)Tj
ET
1 1 1 sc
303.92 458.88 229.92 -121.92 re
f
0.161 0.145 0.149 sc
417.241 426.076 m
416.541 425.676 l
416.541 437.727 l
416.891 437.927 l
417.241 437.727 l
f
418.691 436.676 0.7 -9.55 re
f
427.291 420.276 m
427.291 419.476 l
416.541 425.676 l
417.241 426.076 l
f
437.392 426.076 m
438.092 425.676 l
427.291 419.476 l
427.291 420.276 l
f
437.392 437.727 m
437.742 437.927 l
438.092 437.727 l
438.092 425.676 l
437.392 426.076 l
f
435.192 436.676 0.7 -9.55 re
f
427.291 443.527 m
427.291 444.327 l
437.742 438.327 l
437.742 437.927 l
437.392 437.727 l
f
417.241 437.727 m
416.891 437.927 l
416.891 438.327 l
427.291 444.327 l
427.291 443.527 l
f
BT
7.0003 0 0 7.0003 424.5913 453.2272 Tm
(O)Tj
ET
425.891 452.077 0.7 -8.8 re
f
428.041 452.077 0.7 -8.8 re
f
BT
7.0003 0 0 7.0003 424.5913 405.1251 Tm
(O)Tj
ET
428.041 420.476 0.7 -9.1 re
f
425.891 420.476 0.7 -9.1 re
f
BT
7.0003 0 0 7.0003 445.3921 441.1767 Tm
(OMe)Tj
ET
444.692 442.327 m
445.042 441.727 l
438.092 437.727 l
437.742 437.927 l
437.742 438.327 l
f
BT
7.0003 0 0 7.0003 393.9901 441.1767 Tm
(MeO)Tj
ET
409.491 441.777 m
409.841 442.377 l
416.891 438.327 l
416.891 437.927 l
416.541 437.727 l
f
BT
7.0003 0 0 7.0003 304.7367 391.9746 Tm
(R)Tj
5.2502 0 0 5.2502 309.7921 394.5997 Tm
(1)Tj
ET
321.337 402.375 m
321.687 402.175 l
321.687 401.775 l
313.537 397.075 l
313.187 397.675 l
f
BT
7.0003 0 0 7.0003 331.9878 391.9746 Tm
(R)Tj
5.2502 0 0 5.2502 337.0432 394.5997 Tm
(2)Tj
ET
331.288 397.075 m
330.938 396.475 l
321.687 401.775 l
321.687 402.175 l
322.037 402.375 l
f
BT
7.0003 0 0 7.0003 318.9873 414.4255 Tm
(OH)Tj
ET
321.337 413.275 m
322.037 413.275 l
322.037 402.375 l
321.687 402.175 l
321.337 402.375 l
f
BT
7.0003 0 0 7.0003 498.6441 391.1245 Tm
(R)Tj
5.2502 0 0 5.2502 503.6995 393.7496 Tm
(1)Tj
ET
515.645 401.725 m
515.645 400.925 l
507.444 396.175 l
507.094 396.775 l
f
BT
7.0003 0 0 7.0003 525.8952 391.1245 Tm
(R)Tj
5.2502 0 0 5.2502 530.9506 393.7496 Tm
(2)Tj
ET
525.195 396.175 m
524.845 395.575 l
515.645 400.925 l
515.645 401.725 l
f
BT
7.0003 0 0 7.0003 512.8947 413.5755 Tm
(O)Tj
ET
513.945 412.425 0.7 -11.901 re
f
516.645 412.425 0.7 -11.901 re
f
0.56 w
479.867 404.375 m
345.788 404.375 l
S
485.994 404.375 m
479.086 406.05 l
479.581 405.634 479.867 405.021 479.867 404.375 c
479.867 403.729 479.581 403.116 479.086 402.7 c
f
BT
/TT10 1 Tf
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(1)Tj
/TT8 1 Tf
0.5562 0.0001 TD
(,)Tj
3.0867 -12.8215 TD
(Toluene)Tj
ET
354.389 350.423 m
353.989 349.723 l
347.788 360.423 l
348.638 360.423 l
f
355.739 352.423 m
355.139 352.073 l
350.388 360.273 l
350.988 360.623 l
f
365.939 350.423 m
366.339 349.723 l
353.989 349.723 l
354.389 350.423 l
f
371.739 360.423 m
372.139 360.423 l
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366.339 349.723 l
365.939 350.423 l
f
369.339 360.623 m
369.939 360.273 l
365.189 352.073 l
364.589 352.423 l
f
365.939 370.424 m
366.139 370.774 l
366.589 370.724 l
372.339 360.773 l
372.139 360.423 l
371.739 360.423 l
f
354.389 370.424 m
353.989 371.124 l
365.989 371.124 l
366.139 370.774 l
365.939 370.424 l
f
355.439 368.974 9.45 -0.7 re
f
348.638 360.423 m
347.788 360.423 l
353.989 371.124 l
354.389 370.424 l
f
BT
7.0003 0 0 7.0003 382.0897 357.7231 Tm
(o)Tj
ET
381.29 360.773 m
381.29 360.073 l
372.339 360.073 l
372.139 360.423 l
372.339 360.773 l
f
374.439 379.574 m
374.739 378.874 l
366.589 370.724 l
366.139 370.774 l
365.989 371.124 l
f
BT
7.0003 0 0 7.0003 384.0398 376.5239 Tm
(N)Tj
ET
383.44 379.574 m
383.44 378.874 l
374.739 378.874 l
374.439 379.574 l
f
375.489 377.424 7.95 -0.7 re
f
386.19 391.325 m
386.89 391.025 l
386.89 382.674 l
386.19 382.674 l
f
394.84 399.975 m
395.14 399.275 l
386.89 391.025 l
386.19 391.325 l
f
407.141 399.975 m
406.741 399.275 l
395.14 399.275 l
394.84 399.975 l
f
BT
7.0003 0 0 7.0003 410.4408 386.5743 Tm
(N)Tj
ET
411.191 393.025 m
410.591 392.675 l
406.741 399.275 l
407.141 399.975 l
f
435.942 399.975 m
435.842 399.625 l
435.692 399.275 l
424.091 399.275 l
423.841 399.625 l
423.641 399.975 l
f
444.642 391.325 m
443.942 391.025 l
435.692 399.275 l
435.842 399.625 l
435.942 399.975 l
f
BT
7.0003 0 0 7.0003 441.742 376.5239 Tm
(N)Tj
ET
444.642 382.674 m
443.942 382.674 l
443.942 391.025 l
444.642 391.325 l
f
456.393 379.574 m
456.093 378.874 l
447.342 378.874 l
447.342 379.574 l
f
447.342 377.424 8 -0.7 re
f
464.843 371.124 m
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456.093 378.874 l
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f
459.093 360.423 m
458.693 360.423 l
458.493 360.773 l
464.243 370.724 l
464.693 370.774 l
464.893 370.424 l
f
461.493 360.273 m
460.893 360.623 l
465.593 368.824 l
466.243 368.474 l
f
464.893 350.423 m
464.493 349.723 l
458.493 360.073 l
458.693 360.423 l
459.093 360.423 l
f
476.443 350.423 m
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464.493 349.723 l
464.893 350.423 l
f
465.943 352.573 9.45 -0.7 re
f
482.194 360.423 m
482.994 360.423 l
476.843 349.723 l
476.443 350.423 l
f
476.443 370.424 m
476.843 371.124 l
482.994 360.423 l
482.194 360.423 l
f
475.093 368.474 m
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480.443 360.623 l
479.793 360.273 l
f
464.893 370.424 m
464.693 370.774 l
464.843 371.124 l
476.843 371.124 l
476.443 370.424 l
f
BT
7.0003 0 0 7.0003 443.9921 357.7231 Tm
(O)Tj
ET
450.192 360.073 m
450.192 360.773 l
458.493 360.773 l
458.693 360.423 l
458.493 360.073 l
f
BT
7.0003 0 0 7.0003 410.8408 364.8734 Tm
(Co)Tj
ET
412.041 401.225 1.8 -8.5 re
f
418.191 389.124 m
417.591 389.474 l
423.641 399.975 l
423.841 399.625 l
424.091 399.275 l
f
409.941 367.124 m
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f
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f
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f
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f
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390.74 362.423 l
f
388.64 361.923 m
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386.49 361.373 l
f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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f
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