Acetone → HCID 19352275, compound

Participants

Reaction Conditions

Reaction Steps

12.5 g of anhydrous aluminium chloride (0.094 mole) in 200 ml of methylene chloride are placed into a 3 l round-bottomed flask, under nitrogen atmosphere, cooling to 0° C., then 12.5 g of 4-[2-(2,3-Dimethoxyphenyl)-ethyl]-N-methyl -2,5-oxazolidindione dissolved in 200 ml of methylene chloride are added in about 10 minutes, keeping T<10° C. The mixture is stirred for 30 minutes at T<10° C., then for 1 hour a room temperature. The mixture is cooled again at 0° C. and 200 ml of water are dropped therein, keeping T<20° C., then the mixture is stirred at room temperature for about 1 hour and the organic phase is separated and extracted with water (3×400 ml). The combined aqueous phases are slowly alkalinized with 400 ml of a 20% KHCO3 solution and extracted with 3×400 ml of chloroform. The organic phase is then dried over sodium sulphate, filtered, markedly acidified with methanolic HCl (1M) and evaporated to dryness to obtain a waxy compound, which is taken up into 150 ml of acetone a 50° C., stirred for one hour under stirring and left to stand overnight, then is filtered and dried under vacuum at room temperature. Yield: 8.2 g, 67% (moles); TLC: methylene chloride/methanol, 90/10; Rf=0.35; M.p.=208°-209° C.

Provenance & Evidence