Hydrochloric Acid → (4-Phenylbutyl)phosphonic acid

Participants

Reaction Conditions

Reaction Steps

4-Phenylbutylphosphonous acid (47.19 gm, 0.238 mole) was dissolved in acetone (250 ml) and diluted with water (50 ml). Sodium hydroxide solution (9.5 gm, 0.238 mole) in water (50 ml) was added to it to get pH=7.0. The reaction mixture was cooled to 20° C. and potassium permanganate solution (22.5 gm, 0.142 mole) in water (250 ml) was added to it with stirring and maintaining the temperature around 20°-2 ° C. After the addition (15 minutes), the reaction mixture was stirred for 15 minutes at room temperature, acidified to pH 0 using concentrated HCl acid and saturated sodium bisulphite solution was added to it to get a white cloudy precipitate. Standard extractive workup using ethyl acetate followed by crystallization from ethyl acetate/hexane produced the title compound in 87% (44.16 gm) yield, m.p. 93° C.

Provenance & Evidence