Benzene → HCID 87357320, compound

Participants

Reaction Steps

(R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol (8.3 ml, 66.59 mmol), powdered potassium hydroxide (12 grams) and methanesulfonic acid-2-octyl-dodecyl ester (22.77 grams, 60.50 mmol) were stirred in benzene (250 ml) and refluxed for 5 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 150 ml. The reaction mixture was cooled to room temperature and stirred at room temperature overnight. 200 ml water was added, and the mixture was extracted with diethyl ether (3×200 ml). The combined organic phase was washed with water (200 ml) and the solvent was removed under reduced pressure. The obtained residue was dissolved in 105 ml of a 90:10:5 (v/v) mixture of methanol:water:concentrated hydrochloric acid, and the resulting solution was refluxed for 30 minutes. After cooling to room temperature, water (100 ml) was added. The product was extracted with chloroform (3×100 ml), and washed consecutively with water (100 ml), saturated aqueous solution of sodium carbonate (100 ml) and again with water (100 ml). The solvent was removed under reduced pressure, and the crude product was purified by chromatography on a silica gel (400 grams) column. 17 grams of pure 1-(2-octyl)dodecyl-glycerol was eluted by chloroform followed by a mixtures of chloroform and 10%-30% ethyl acetate as a colorless oil. The yield was 75.5%.

Provenance & Evidence