Diethyl chlorophosphate → 4-(2,5-Dimethoxycinnamoylamino)-2,6-dimethylphenol

Participants

Reaction Steps

Under ice-cooling, 4.16 g of 2,5-dimethoxycinnamic acid is dissolved in 50 ml of acetonitrile, and to the resultant solution are added 3.03 g of triethylamine, then 4.13 g of diethylphosphorochloridate. After the mixture is stirred for one hour, 2.74 g of 4-amino-2,6-dimethylphenol is added and the reaction mixture is stirred at room temperature. After completion of the reaction, ice chips are added, and then 5 % aqueous sodium hydrogen carbonate solution is added. The crystals precipitated are collected by filtration, and washed with isopropyl ether. The crystals obtained are recrystallized form ethyl acetate to give 4.64 g of 4-(2,5-dimethoxycinnamoylamino)-2,6-dimethylphenol as white crystals.

Provenance & Evidence