Reaction #94547

Reaction equation

Tri-n-butyl phosphine

monochloroacetic acid

phosphine

→

Tri-n-butyl(carboxymethyl)phosphonium Chloride

Solvents

methanol

Conditions

Workup

1. 1
   Otherdid not exceed about 30° C
2. 2
   OtherThe methanol solvent was subsequently evaporated under reduced pressure
3. 3
   Otherleaving a colorless viscous liquid whose infrared spectrum and elemental analysis

Procedure

Tri-n-butyl phosphine (4.04 g, 0.02 mole) was added dropwise to a rapidly stirred solution of monochloroacetic acid (1.85 g, 0.02 mole) and 3.2 ml of methanol. The addition of the phosphine was at a rate such that the reaction temperature did not exceed about 30° C. The methanol solvent was subsequently evaporated under reduced pressure leaving a colorless viscous liquid whose infrared spectrum and elemental analysis corresponded to a compound of the formula

Source