Sodium Hydroxide → 5-(Benzyloxy)-2-sulfanylphenol

Participants

Reaction Steps

A mixture of 6-benzyloxy-1,3-benzoxathiol-2-one (35 g), aqueous sodium hydroxide solution (200 mL; 2 N) and methanol (50 mL) is stirred at ambient temperature for 16 hours and then it is heated at reflux for 30 minutes. The reaction mixture is then evaporated to dryness and the residue is acidified to pH 1 by treatment with concentrated hydrochloric acid (20 mL). The residue is diluted with water (200 mL) and then extracted with diethyl ether (3×200 mL). The combined organic extracts are washed with brine (100 mL), dried over magnesium sulphate, filtered and concentrated in vacuo, to give 5-benzyloxy-2-mercaptophenol, in the form of a yellow oil which solidified on standing overnight.

Provenance & Evidence