Thiobenzoic acid

clear yellow to brown liquid

Organic intermediate.

Journal of the American Chemical Society, 95, p. 3440, 1973 DOI: 10.1021/ja00791a092
Organic Syntheses, Coll. Vol. 4, p. 924, 1963

To a solution of N,N-dimethylthioformamide (1.0 mmol) in THF (1.0 mL) was added a 1.0 M phenyl lithium cyclohexane-Et2O solution (1.0 mL, 1.0 mmol) at -78C. After the addition was complete, the mixture was stirred for 0.5 h at room temperature. A 0.93 M THF solution of phenylmagnesium bromide (1.0 mmol) was added to the mixture at room temperature. This mixture was stirred at reflux for 2 hours. Benzoyl chloride (1.0 mmol) was added to the mixture. The reaction mixture was stirred again for 2 hours at room temperature. The resulting mixture was poured into saturated aqueous NH4Cl solution. The organic and aqueous layers were separated. The aqueous layer was acidified with aqueous HCl solution (1N, 10 mL). Extracted the aqueous layer with Et2O to obtain organic layer II. dried organic layer II on MgSO4. vacuum concentrated organic layer II to obtain thiobenzoic acid.