Bromoacetic Acid → (Diethoxyphosphinyl)acetic acid

Participants

Reaction Steps

A mixture of 4.0 ml (0.031 mole) of diethyl phosphite, 6.68 g (0.093 mole) of 94% sodium ethoxide, and 4.32 g (0.031 mole) of bromoacetic acid in 50 ml of absolute ethanol was heated under reflux for 1 h. Solvent was removed at reduced pressure, and the residual solid was triturated with ethyl acetate and 15 ml of conc hydrochloric acid with shaking and portionwise addition of water until all the solid was dissolved. The ethyl acetate layer was separated, dried (over MgSO4), and evaporated to give 9.4 g of residual liquid diethyl carboxymethylphosphonate; 1H NMR spectrum confirmed the structure of this compound which is disclosed by Martin and Griffin, J. Org. Chem., 30, 4034-4038 (1965).

Provenance & Evidence