Benzyl mercaptan → Methyl 2-benzylthio-3-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

In a 5 1 pot was charged 483 g of methyl 2-nitro-3-methylbenzoate, 319 g benzyl mercaptan and 100 mL dimethyl formamide. Upon cooling to 0° C., a solution of 321 g potassium tert-butoxide in 1500 mL dimethyl formamide was added dropwise over 2.5 hours at 0°-5° C. The reaction mixture was stirred at 0° C. for 1.5 hours and then at room temperature overnight. The reaction was quenched by addition of 1 1 water and worked up by extraction with 2 1 methylene chloride. Upon washing with water (3×1 1), the methylene chloride layer was dried over MgSO4, filtered and rotovapped to give 517 g of crude methyl 2-benzylthio-3-methylbenzoate (77% yield) as a liquid.

Provenance & Evidence