3-Chloro-1,2-propanediol → HCID 70190292, compound

Participants

Reaction Conditions

Reaction Steps

240 g (0.84 mol) of methyl Z-16-hydroxyhexadec-11-enoate and 50 g of potassium hydroxide were dissolved in 500 ml of methanol in a 3 liter flask. The mixture was heated to reflux temperature for 2 hours. Then, the methanol was distilled off and 800 ml of glycerol were added to the residue. 250 ml of glycerol were distilled off (150° C., 3 mmHg). 160 g (1.45 mol) of 3-chloropropane-1,2-diol were added slowly at 150° C. and the mixture was stirred at this temperature for 1 hour. Then, 200 ml of a mixture of 3-chloropropane-1,2-diol and glycerol were distilled off (120-148° C. 3 mmHg, internal temperature 160-170° C.). The mixture was cooled to 60° C. and treated at this temperature with 25 ml of 5.4M ethanolic sodium methanolate solution. The mixture was distilled further (3 mmHg, 180-200° C.) and glycerol was replaced continuously. After 950 ml of a two-phase mixture had been distilled off the residue was extracted with hexane. After distillation there were obtained 167 g (78%) of 12Z-oxacycloheptadec-12-en-2-one, were obtained having the following characteristics: Z/E=91/9;

Provenance & Evidence