Solketal → 3-[(12-Cyclohexyldodecyl)oxy]propane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

A mixture of 40.8 g (0.123 mole) of 12-cyclohexyldodecyl bromide, 22.7 g (0.172 mole) of 1,2-isopropylideneglycerol, 1.0 g of cetyltrimethylammonium chloride and 27.6 g (0.344 mole) of 50% aqueous solution of sodium hydroxide was stirred at 80° C. for 10 hours. Then to the reaction mixture was added 200 ml of hexane, and the resulting mixture was washed with water, and dried (MgSO4), followed by evaporation of the solvent under reduced pressure. To the residue were added 200 ml of methanol and 4 ml of 6N hydrochloric acid, and the mixture was heated under reflux for 10 hours and then cooled. The precipitated colorless crystals were collected by filtration, washed with hexane, and dried, to give 10.1 g of the above-captioned compound. The mother liquid was further cooled, to give 20.8 g of the second crystals. Overall yield: 30.9 g (74%)

Provenance & Evidence