Ring-opening of thiirane with a thiol; 4-(2-Mercaptoethylsulfanyl)phenol
SyntheticPage 447
DOI:
10.1039/SP447
Submitted Jul 25, 2010, published Jul 27, 2010
Christopher Cooksey (
rsc@chriscooksey.demon.co.uk)
A contribution from
QUINTOX group
Chemicals Used
Ethylene sulfide (Aldrich)
4-Mercaptophenol (Aldrich)
Triethylamine
Procedure
Ethylene sulfide (3.2 cm3, 0.053 mol) was added to a magnetically stirred mixture of 4-mercaptophenol (6.3 g, 0.05 mol) and Et3N (3 drops) heated on a water bath at 40 – 45 ºC over a period of 1 h. After the addition was complete heating was continued for a further 0.5 h. The product was distilled, b.p. 100 – 120 ºC/0.01 mm, to give a colourless oil (4.0 g, 43%).
Author's Comments
This reaction was based on the recipe for the addition of
ethylene oxide to
4-mercaptophenol (Dachs NW
et al) which gave
4-(2-hydroxy-ethylsulfanyl)-phenol.
Page 446
Data
δH (CDCl3), 7.27d (2H), 6.70d (2H), 5.62brs (1H, OH), 2.39 – 3.10m (4H), 1.67dd (1H, 7.4, 9.0, SH)
δC (CDCl3), 154.94s, 134.14d (2C), 124.71s, 116.12d (2C), 39.61t, 24.03t
EI MS, m/z (%), 186 (14), 140 (26), 126 (100)
mass = 186.0196, calc for C
8H
10OS
2 186.0174
Lead Reference
Naish-Byfield S, Cooksey CJ, Latter AM, Johnson CI, Riley PA, Melanoma Res. 1991, 1(4), 273 – 287, PMID: 1823634
Other References
Dachs NW, Gruber R, US patent, 1972, 3646220
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Keywords: nucleophilic, sulphides