Triphenylphosphine → (3-Carboxypropyl)(triphenyl)phosphanium bromide

HRID 1287339Notes

Reaction equation

HRID 1287339 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]>C1C=CC=CC=1>[Br-:20].[C:24]([CH2:23][CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 758094-Bromobutyric acid

Product 1

HCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Refer to Chart A. 3-Carboxypropyltriphenylphosphonium bromide is prepared by heating triphenylphosphine (156.8 g.) and 4-bromobutyric acid (100 g.) in 125 ml. of benzene at reflux for 18 hrs. The crystalline product is filtered off, washed with benzene, and recrystallized from ethanolacetonitrile-ether, 150 g., m.p. 247°-249° C.

Workup

  1. filtrationThe crystalline product is filtered off
  2. washwashed with benzene
  3. customrecrystallized from ethanolacetonitrile-ether, 150 g

Sources & evidence

ORD record
ord-d83b62b8796347d89d44ba4d571b4df5
Source dataset
uspto-grants-1976_10
Patent number
US03984457

Reaction notes

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