Triphenylphosphine → 5-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromide

HRID 463044Notes

Reaction equation

HRID 463044 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[Br-:1].[C:7]([C:6]([CH3:11])([CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10036524HCID 10036524, compound

Product 1

HCID 861086235-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromideYield 58.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Bromo-2,2-dimethylhexanoic acid (3.8 g, 17 mmole) and triphenylphosphine (4.9 g, 18.7 mmole) were dissolved in acetonitrile (30 ml), and the solution was heated under reflux for 20 hours. After the completion of the reaction, the solvent was removed under reduced pressure, and the residue was treated with toluene, followed by thorough stirring. The insolubles were seperated from the toluene solution, and crystallized from ethyl acetate to give 5-carboxy-5,5-dimethylpentyltriphenylphosphonium bromide (4.8 g, 58%) [NMR (δ value): 1.10 (6H,s), 1.4-1.6 (6H), 3.4-3.8 (2H)].

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 20 hours
  3. customAfter the completion of the reaction
  4. customthe solvent was removed under reduced pressure
  5. additionthe residue was treated with toluene
  6. customThe insolubles were seperated from the toluene solution
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-235270cfcd6843f9990fd14a6abeacb6
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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