Sodium Hydroxide → HCID 54402218, compound

Participants

Reaction Steps

A solution of 3.5 g (25 mmol) of diethyl phosphite in 6 ml of carbon tetrachloride was added dropwise, while cooling with ice, to a mixture of 7 g (20 mmol) of 4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propenyl]-benzyl alcohol, 12 ml of carbon tetrachloride, 0.16 g of tetrabutylammonium bromide and 6 ml of 50% strength sodium hydroxide solution. The mixture was stirred for 3 days at room temperature, then extracted with 30 ml of methylene chloride, the organic phase was washed with 10 ml of 2% strength hydrochloric acid and twice with 10 ml of water each time, and was dried over Na2SO4 and evaporated down. The residue was recrystallized from pentane and once again from petroleum ether, to give 0.3.g of the title compound of melting point 70°-74° C., which was 98% pure according to HPLC (C18 reverse phase; hexane/ethanol/0.1% strength acetic acid; 100 ml/min.).

Provenance & Evidence