Triphenylphosphine → HCID 86108424, compound

HRID 463050Notes

Reaction equation

HRID 463050 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([OH:9])=[O:8].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Br-:1].[C:7]([CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][CH2:4][CH2:3][CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 19431593HCID 19431593, compound

Product 1

HCID 86108424HCID 86108424, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

6-Bromo-2-phenylhexanoic acid (16 g, 59 mmole) and triphenylphosphine (20 g, 76 mmole) were dissolved in acetonitrile (100 ml), and the solution was heated at 100° C. for 18 hours. After the completion of the reaction, the solution was cooled and the solvent removed under reduced pressure. The residue was washed three times with toluene, whereby crystals separated out. The crystals were recrystallized from ethyl acetate to give 5-carboxy-5-phenylpentyltriphenylphosphonium bromide (21 g, 67%, m.p. 210°-215° C.).

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe solution was cooled
  3. customthe solvent removed under reduced pressure
  4. washThe residue was washed three times with toluene, whereby crystals
  5. customseparated out
  6. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5f4a8944e2b74459b3c6d89f53e204ac
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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