Hexane → 4-((2-Hydroxyethyl)thio)phenol

Participants

Reaction Conditions

Reaction Steps

A solution of 5.0 g (35.7 mmol) 4-mercaptophenol in 50 ml methyl alcohol was treated at −5° C. dropwise over a period of 30 min with 39.2 ml (39.2 mmol) aqueous NaOH 1N and stirred 1 h at −5° C. Afterwards a solution of 5.2 ml (39.2 mmol) 2-bromo ethanol in 16.5 ml methyl alcohol was added at −5° C. dropwise over a period of 15 min. The reaction mixture was stirred for 21 h at room temperature, concentrated and the residue treated with 10 ml water and 30 ml tBME. After extraction and phase separation, the organic phase was washed with 20 ml saturated NaHCO3 and 20 ml brine. The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure to yield 6.03 g crude product. The crude product was dissolved in 18 ml tBME at 40° C. and subsequently treated dropwise with 25 ml hexane. The so formed suspension was stirred 16 h at room temperature and 1 h at 4° C. The crystals were separated on a filter funnel and washed with 5 ml hexane (4° C.) to yield 4.8 g (77.7%) product as white crystals.

Provenance & Evidence