Toluene → Phosphonium, (8-carboxyoctyl)triphenyl-, bromide

HRID 1091068Notes

Reaction equation

HRID 1091068 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[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:31]1(C)C=CC=CC=1>>[Br-:1].[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:31][P+:18]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5482758-Bromooctanoic acid

Product 1

HCID 10918084Phosphonium, (8-carboxyoctyl)triphenyl-, bromide

Procedure

Dissolve 8-bromooctanoic acid (1.0 g) in anhydrous toluene (3 mL) and add triphenylphosphine (1.21 g). Heat to reflux overnight. Separate the lower phase crystallize (ethanol/ethyl ether) to give (8-carboxyoctyl)triphenylphosphonium bromide (1.0 g).

Workup

  1. temperatureHeat
  2. temperatureto reflux overnight
  3. customSeparate the lower phase
  4. customcrystallize (ethanol/ethyl ether)

Sources & evidence

ORD record
ord-b0a8b9a6a261415eb34533de797101b5
Source dataset
uspto-grants-1992_01
Patent number
US05084461

Reaction notes

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