Dichloroacetic Acid → HCID 21163202, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 13 ml of dichloroacetic acid and 75 ml of dioxane was added over 40 minutes to a suspension of 1.6 g of dibenzo-18-courone-6, 20.2 g of sodium hydride as a 50% oil suspension and 250 ml of dioxane and then a solution of 30 g of the product of Step A in 150 ml of dioxane was added thereto at 60° C. over one hour. The mixture was heated at 90° C. for 2 hours, was cooled and poured into 500 ml of ice. The aqueous phase was washed 3 times with 300 ml of ether, was acidified with concentrated hydrochloric acid and was extracted 3 times with 300 ml of ether. The ether phase was extracted 4 times with 100 ml of aqueous sodium bicarbonate solution and the combined aqueous phase was acidified with hydrochloric acid and was extracted 3 times with 300 ml of ether. The ether phase was washed with water until the wash water was neutral, dried over magnesium sulfate and was evaporated to dryness under reduced pressure to obtain 28 g of raw 4,6-dimethyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of 2 diastereoisomeric racemates).

Provenance & Evidence