Triethyl phosphonoacetate → (Diethoxyphosphinyl)acetic acid

Participants

Reaction Steps

Ethyl diethylphosphonoacetate (100 g, 446 mmol) was dissolved in ethanol (275 ml), and after adding dropwise a 2 mol/l aqueous sodium hydroxide solution (275 ml, 550 mmol) while stirring and cooling with ice, it was stirred at room temperature for 1 hour. The reaction solution was then concentrated under a reduced pressure, and the concentrate was made acidic by concentrated hydrochloric acid while cooling with ice. Extractions into ethyl acetate (200 ml×4), chloroform (100 ml×2) and 5% methanol/chloroform (250 ml×2) were then performed. The combined organic layers were then dried over anhydrous sodium sulfate, and after filtering, the filtrate was concentrated under a reduced pressure. 89 g (quantitative) of the title compound was thereby obtained as a colorless, oily substance.

Provenance & Evidence