Ethanol → 4-(Diethylphosphono)phenylmethanol

Participants

Reaction Steps

To a stirred solution of 3.0 grams (0.01 mole) of 4-(diethylphosphono)phenylmethyl acetate in 10 mL of tetrahydrofuran was added a solution of 0.4 gram (0.01 mole) of sodium hydroxide in 1 mL of water. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for one hour. After this time 5 mL of ethanol was added, and the reaction mixture was warmed to reflux, where it stirred for one hour. The reaction mixture was poured into a stirred mixture of water and ethyl acetate. The organic layer was separated and dried with magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 2.1 grams of 4-(diethylphosphono)phenylmethanol. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence