Chloroacetic Acid → Tributyl(carboxymethyl)phosphanium chloride

HRID 2071582

Reaction equation

HRID 2071582 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][CH2:15][C:16]([OH:18])=[O:17].P>CO>[Cl-:14].[CH2:10]([P+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 13831TributylphosphineHCID 24404Phosphine

Product 1

HCID 23463525Tributyl(carboxymethyl)phosphanium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

Workup

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

Sources & evidence

ORD record
ord-afffb501f4614600a685ce6049288ea0
Source dataset
uspto-grants-1977_09
Patent number
US04048141

Linked notes

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