Reaction #94546

Reaction equation

Tri-n-butyl phosphine

2-chloropropanoic acid

phosphine

→

Tri-n-butyl(1-carboxyethyl)phosphonium Chloride

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturewas maintained at a rate such that the temperature
2. 2
   Otherdid not exceed about 35° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   Otherthe acetone solvent was removed under reduced pressure
5. 5
   Otherleaving a viscous liquid

Procedure

Tri-n-butyl phosphine (20.27 g, 25 ml, 0.1 mole) was added dropwise to a rapidly stirred solution of 2-chloropropanoic acid (10.85 g, 9.1 ml, 0.1 mole) in 31 ml of acetone. The reaction was, of course, exothermic, and the addition of the phosphine was maintained at a rate such that the temperature did not exceed about 35° C. After the addition was complete, the acetone solvent was removed under reduced pressure leaving a viscous liquid having an infrared spectrum and elemental analysis corresponding to the formula ##STR13##

Source