Acetonitrile → (4-Carboxybutyl)triphenylphosphonium bromide

HRID 617071Notes

Reaction equation

HRID 617071 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(#N)C>C1C=CC=CC=1>[Br-:1].[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 163685-Bromovaleric acid

Product 1

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 103 g. of 5-bromovaleric acid and 152 g. of triphenylphosphine in 400 ml. of acetonitrile is refluxed for 48 hours, cooled, diluted with 100 ml. of benzene and allowed to crystallize. The crystals are filtered, washed with benzene and ether, to yield colorless material, m.p. 207°-209° C.

Workup

  1. additionA mixture of 103 g
  2. temperaturecooled
  3. additiondiluted with 100 ml
  4. customto crystallize
  5. filtrationThe crystals are filtered
  6. washwashed with benzene and ether
  7. customto yield colorless material, m.p. 207°-209° C.

Sources & evidence

ORD record
ord-39b1b88194b04b9d8d2d34e9c2c0fd48
Source dataset
uspto-grants-1978_02
Patent number
US04076947

Reaction notes

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