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

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-benzyloxy-benzo[1,3]oxathiol-2-one (24.33 g, 94.29 mmol) in dioxane (1000 mL) and add a KOH solution (94.29 mL, 188 mmol, 2M in water) with stirring. Flush the flask with N2 and then heat the reaction mixture to 80° C. for 2 hours. Cool the reaction mixture to room temperature and remove the solvent under reduced pressure. Adjust the pH to <2 with HCl (200 mL, 1.0 M in water). Extract the aqueous layer with EtOAc (3×500 mL). Combine the organic layers and dry with Na2SO4, filter and concentrate to give 17.8 g of 5-benzyloxy-2-mercapto-phenol (81.4%).

Provenance & Evidence