Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2003(1): 0112-0116
DOI: 10.1055/s-2003-36251
DOI: 10.1055/s-2003-36251
PAPER
© Georg Thieme Verlag Stuttgart · New York
Practical and Scaleable Syntheses of 3-Hydroxythiophenol
Further Information
Received
27 June 2002
Publication Date:
18 December 2002 (online)
Publication History
Publication Date:
18 December 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200301/lookinside/thumbnails/10.1055-s-2003-36251-1.jpg)
Abstract
3-Hydroxythiophenol is a versatile intermediate for the synthesis of medicinal and heterocyclic compounds. Two novel and practical syntheses of 3-hydroxythiophenol are achieved using readily available and inexpensive starting materials. An overall cost comparison of these syntheses is also given.
Key words
3-hydroxythiophenol - Grignard reactions - diazo compounds - sulfur - practical synthesis
-
2a
Palkowitz AD.Glasebrook AL.Thrasher KJ.Hauser KL.Phillips DL.Muehl BS.Sato M.Shetler PK.Cullinan GJ.Pell TR.Bryant HU. J. Med. Chem. 1997, 40: 1407 -
2b
Sindelar K.Pomykacek J.Svatek E.Valchar M.Dobrovsky K.Metysova J.Polivka Z. Collect. Czech. Chem. Commun. 1991, 56: 459 -
2c
Meurer K.Vogtle F.Mannschreck A.Stuhler G.Puff H.Roloff A. J. Org. Chem. 1984, 49: 3484 - 3
Zincke T.Ebel C. Berichte 1914, 47: 923 - 4
Watson ER.Dutt S. J. Chem. Soc. 1922, 121: 2414 -
5a
Tarbell DS.Fukushima DK. Org. Synth., Coll. Vol. III John Wiley & Sons; New York: 1955. p.809 -
5b (b)
Tarbell DS.Fukushima DK. Org. Synth., Coll. Vol. III John Wiley & Sons; New York: 1955. p.1050 - 6
Cabiddu S.Melis S.Piras PP.Sotgiu F. Synthesis 1982, 583 -
7a
Voronkov MG.Deryagina EG.Klochkova LG. J. Org. Chem. USSR (Engl. Transl.) 1977, 13: 969 -
7b
Shagun LG.Deriglazova ES.Kashik TV.Deryagina EN.Voronkov MG. J. Org. Chem. USSR (Engl. Transl.) 1978, 14: 173 - 8
March J. In Advanced Organic Chemistry John Wiley & Sons; New York: 1992. 4th ed.. p.613 - 9 The yield of the Grignard reagent
was typically in the range of 75-80% based on
3-trimethylsiloxylbromobenzene as determined by titration following
a method of Watson and Eastham, see:
Watson SC.Eastham JF. J. Organomet. Chem. 1967, 9: 165 - 11
Sheppard WA. Org. Synth., Coll. Vol. V John Wiley & Sons; New York: 1973. p.843 -
12a
Gilman H.Schulze F. J. Am. Chem. Soc. 1925, 47: 2002 -
12b
Gilman H.Heck LL. J. Am. Chem. Soc. 1930, 52: 4949
References
Author for correspondence. Current address: Department of Chemistry, Bayer Research Center, Pharmaceutical Division, 400 Morgan Lane, West Haven, CT 06516. E-mail: mingbao.zhang.b@bayer.com; telephone +1(203)8125906; fax +1(203)8163505
10No attempt was made to assess the stability and energy of decomposition of the di-diazonium salt intermediate.