Potassium Hydroxide → HCID 19814654, compound

Participants

Reaction Steps

A mixture of 12 g of KOH pellets, 150 mL of methanol and 24.9 g of methyl 2-hydroxy-3-methylbenzoate (I) was stirred at room temperature for 0.5 hours. The mixture was then cooled to 5° C. and 19 g of dimethylthiocarbamoyl chloride was added in one portion. An exotherm of 5° C. was observed. The resulting mixture was stirred for 2 hours and then added to 300 mL of ice water. After filtering, the crystalline product was washed with water and oven dried to yield 30-35 g of methyl 2-[(dimethyl-amino)thioxomethoxy]-3-methylbenzoate II, (E is O, W is S) in 80-92% yield, mp 94-96° C.

Provenance & Evidence