Water → HCID 12812398, compound

Participants

Reaction Steps

A solution of 9.95 g of 5-chloro-2-hydroxy-α-methyl-α-phenyl-benzene-methanol in 150 ml of anhydrous toluene was added dropwise at room temperature to a mixture of 4 g of sodium amide and 50 ml of anhydrous toluene and the mixture was refluxed for 6 hours and cooled to room temperature. 10.25 g of potassium dibromoacetate were added thereto and the mixture was refluxed for another 6 hours and cooled. 200 ml of water were added thereto and the organic phase was decanted and extracted twice with 80 ml of water. The aqueous phase was washed twice with 80 ml of ether and was acidified with 40 ml of 2 N hydrochloric acid. The resulting precipitate was extracted 3 times with 100 ml of ether and the ether extracts were washed twice with 80 ml of water and extracted with 50% of an aqueous 5% sodium bicarbonate solution. The aqueous phase was washed 3 times with 80 ml of ether and acidified with 90 ml of 2 N hydrochloric acid solution. The mixture was extracted 4 times with 100 ml of ether and the combined ether extracts were washed with water, dried over magnesium sulfate, treated with activated carbon and evaporated to dryness under reduced pressure to obtain 7.85 g of raw product. The latter was taken up in hexane and vacuum filtered and the recovered crystals were dried to obtain 6 g of 6-chloro-4-methyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of two racemates diastereoisomers) melting at 144° C.

Provenance & Evidence