2-Chloropropionic acid → Tri-n-butyl(1-carboxyethyl)phosphonium Chloride

HRID 2071581Notes

Reaction equation

HRID 2071581 reaction equation
[CH2:1]([P:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Cl:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17].P>CC(C)=O>[Cl-:14].[CH2:10]([P+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH:15]([C:16]([OH:18])=[O:17])[CH3:19])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 117342-Chloropropionic acidHCID 13831TributylphosphineHCID 24404Phosphine

Product 1

HCID 18533282Tri-n-butyl(1-carboxyethyl)phosphonium Chloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 ##STR14##

Workup

  1. temperaturewas maintained at a rate such that the temperature
  2. customdid not exceed about 35° C
  3. additionAfter the addition
  4. customthe acetone solvent was removed under reduced pressure
  5. customleaving a viscous liquid

Sources & evidence

ORD record
ord-f7d8a088d7bc45dea7040b74767eb97e
Source dataset
uspto-grants-1977_09
Patent number
US04048141

Reaction notes

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