Dichloroacetic Acid → HCID 21163200, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 17 g of dichloroacetic acid in 180 ml of dioxane was added dropwise with stirring to a suspension of 14.9 g of sodium hydride as 50% oil suspension, 1.1 g of dibenzo-18-courone-6 and 160 ml of dioxane and then a solution of 21.5 g of the product of Step A in 220 ml of dioxane was added. The reaction mixture was heated at 90° C. for 3 hours, was cooled and was poured into ice. The aqueous phase was washed with 300 ml of ether, was acidified with 30 ml of concentrated hydrochloric acid and was extracted 3 times with 200 ml of ether. The ether phase was washed twice with 100 ml of water and was extracted twice with 250 ml of aqueous 5% sodium bicarbonate solution. The aqueous phase was washed with 100 ml of ether, acidified with 40 ml of concentrated hydrochloric acid and was extracted 3 times with 250 ml of ether. The combined organic phases were washed with water until the water was neutral, dried over magnesium sulfate and evaporated under reduced pressure to obtain 29.8 g of raw 6-methoxy-4-methyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of 2 diastereoisomeric racemates).

Provenance & Evidence