Hydrochloric Acid → (4-TERT-BUTYLPHENYL)THIO]ACETIC ACID

Participants

Reaction Conditions

Reaction Steps

Sodium chloroacetate (6.29 g, 54 mmol) was added in portions to a solution of 4-t-butylbenzenethiol (9.0 g, 54 mmol) in a 30% (w/v) aqueous solution of sodium hydroxide (10.8 ml, 81 mmol) with stirring at 80° C. When the addition was complete, stirring was continued for an additional 2 hours at 80° C., during which time a thick white precipitate had formed. The reaction mixture was added to water (200 ml) and was acidified to pH 2 by the addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate. The combined extracts were then extracted with a 10% (w/v) aqueous solution of potassium carbonate. The aqueous extracts were acidified to pH 2 by the addition of 2M hydrochloric acid and again extracted with ethyl acetate. These combined extracts were dried (MgSO4) and the solvent was removed by evaporation to give 2-(4-t-butylphenylthio)acetic acid (B) as a straw coloured oil (9.07 g); which had a satisfactory NMR spectrum.

Provenance & Evidence