Hydrochloric Acid → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Participants

Reaction Steps

70 g (0.7 mol) of succinic anhydride and 96.6 g (0.7 mol) of veratrole were dissolved in 2,000 ml of methylene chloride, and 237 g (1.75 mol) of anhydrous aluminum chloride was added thereto at room temperature. The mixture was stirred at the same temperature for 6 hours. The reaction solution was left to stand for 15 hours. Then, 1,600 ml of 6N hydrochloric acid was dropwise added to the reaction solution under stirring and the mixture was further stirred for one hour. The organic layer was separated, and 300 ml of water was added thereto. The mixture was adjusted to pH7.5 with a saturated sodium bicarbonate aqueous solution. The aqueous layer was separated and adjusted to pH2.5 with 6N hydrochloric acid. The aqueous layer was left to stand in a refrigerator for two days. Then, the precipitated crystals were collected by filtration, washed with water and dried to obtain 106.8 g (yield: 64%) of 3-(3,4-dimethoxybenzoyl)propionic acid.

Provenance & Evidence