Phthalide → 2-[(Phenylsulfanyl)methyl]benzoic acid

Participants

Reaction Steps

A mixture of 67.1 gm of phthalide, 51.3 ml of thiophenol, 35.1 gm of potassium methylate and 250 ml of methanol was refluxed. Subsequently, the obtained 2-(phenylmercapto-methyl) -benzoic acid (yield: 78% of theory, m.p. 108°-110° C.) was esterified with methanol/thionylchloride by standing at -40° C. After standing overnight at room temperature, methyl 2-(phenylmercapto-methyl)-benzoate (yield: 89% of theory, b.p. 145° C. at 0.07 mm Hg) was obtained, which was converted into 2-(phenylmercapto-methyl)-phenyl carbinol (yield: 97% of theory, m.p. 64°-65° C.) by reduction with lithium aluminum hydride in diethyl ether.

Provenance & Evidence