Sodium Hydroxide → 4-((2-Hydroxyethyl)thio)phenol

Participants

Reaction Steps

To a solution of 10.9 g 4-hydroxythiophenol (87 mmol) in 200 ml MeOH was added at 0-5° C. 87 ml 1N NaOH (87 mmol). After the reaction mixture was stirred for 10 min 6.1 ml bromoethanol (86 mmol) dissolved in 100 ml MeOH was added. The reaction mixture was stirred for 3 h at r.t. and the methanol was partly removed under reduced pressure. The residue was poured to a 1:1 mixture of ethyl acetate and saturated NaHCO3−solution and the organic phase was separated, dried over MgSO4, filtrated and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel (ethyl acetate/hexane 3/2 to 2/1) to give 13.4 g product (78.7 mmol, 91%) as a white solid.

Provenance & Evidence