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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


			Reaction Scheme: Ring-opening of thiirane with a thiol

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 C8H10OS2 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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Get structure file (.cdx, .sk2, .mol)

Keywords: nucleophilic, sulphides

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