p-Nitroacetophenone → 1-(4-Nitrophenyl)ethan-1-ol

Participants

Reaction Steps

Poly(4-(1-(4-nitrophenyl)ethyloxycarbonyloxystyrene (FIG. 7A) was prepared from poly(4-hydroxystyrene), available from the Maruzen Oil Company, by treatment with trichloromethyl chloroformate and 1-(4-nitrophenyl)ethanol. Specifically, a solution of 4-nitroacetophenone in ethanol was treated with sodium borohydride at about 0° C. for about 4 hours, then quenched by the addition of water. Extraction with ethyl acetate followed by drying and concentration provided crude 1-(4-nitrophenyl)ethanol, which was purified by recrystallization. A solution of 1-(4-nitrophenyl)ethanol in tetrahydrofuran (THF) was added to a solution of excess trichloromethyl chloroformate and triethylamine in THF, stirred at reflux for about 2 hours, filtered to remove the solids, and concentrated under vacuum. The resulting oil was dissolved in THF and added to a solution of poly(4-hydroxystyrene), 4-dimethylaminopyridine, and triethylamine in THF. This mixture was stirred for about 18 hours at about 20° C., filtered, then concentrated. The residue was dissolved in methylene chloride, treated with aqueous sodium bicarbonate solution, and the polymer was precipitated by addition into methanol.

Provenance & Evidence