Benzyl Chloride → 2-Benzyloxy-3-(12-cyclohexyldodecyloxy)propanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 35 g (4.6 mmole) of 1-(12-cyclohexyldodecyloxy)-3-trityloxy-2-propanol prepared in Reference Example 11, 8.7 g (69 mmole) of benzyl chloride, 0.5 g of cetyltrimethylammonium chloride, 7.4 g (92 mmole) of 50% aqueous sodium hydroxide solution and 50 ml of THF was stirred at 60° C. overnight. To the reaction mixture were further added 7.4 g (92 mmole) of 50% aqueous sodium hydroxide solution and 8.7 g (69 mmole) of benzyl chloride, and the resulting mixture was stirred overnight. THF was distilled off from the mixture, and 100 ml of hexane was added to the residue. The mixture was washed with water and then hexane was distilled off. To the residue were added 120 ml of dioxane and 60 ml of 1N hydrochloric acid, and the mixture was stirred at 80° C. for 5 hours. After the mixture was cooled and neutralized with sodium bicarbonate, 100 ml of ethyl acetate was added to the mixture. The organic layer was washed with water and dried (MgSO4), and then the solvent was distilled off. The residue was allowed to stand at room temperature overnight. A small amount of hexane was added to the residue and the deposited tritylalcohol was filtered off. The filtrate was subjected to column chromatography on silica gel (500 g) and eluted with hexane-ethyl acetate (9:1) to give 9.0 g (yield: 45%) of the above-mentioned compound as a colorless oil.

Provenance & Evidence