Toluene → 2-(N,N-diethylcarbamoyloxy)-6-methoxytoluene

Participants

Reaction Conditions

Reaction Steps

A solution of 3.15 g (22.8 mmol) of 2-hydroxy-6-methoxytoluene in 16 mL acetonitrile was added with 3.50 g (25.1 mmol) of potassium carbonate and 3.4 g (25.1 mmol) of diethylcarbamoyl chloride and heated and stirred on a 100° C. oil bath for 59 minutes. After addition of 0.6 g (4.4 mmol) of diethylcarbamoyl chloride and heated for 38 minutes, while stirring on an ice-water bath, 30 mL of toluene and 30 mL of water, were added into the reaction mixture, and the mixture was stirred for 20 minutes, transferred to a separatory funnel and settled. The aqueous layer was separated and discarded and after the organic layer was washed with 10 mL of 2 N aqueous sodium hydroxide and 10 mL of water twice, and the solvent was evaporated to obtain 5.58 g of the crude title compound. Since the mixture solidified, a part thereof was obtained as seed crystals.

Provenance & Evidence