Triphenylphosphine → Phosphonium, (10-carboxydecyl)triphenyl-, bromide

HRID 345208Notes

Reaction equation

HRID 345208 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br-:1].[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1781211-Bromoundecanoic acid

Product 1

HCID 11432504Phosphonium, (10-carboxydecyl)triphenyl-, bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 303 g (1.14 mol) of 11-bromoundecanoic acid and 303 g (1.16 mol) of triphenylphosphine in 3L of toluene was stirred and refluxed under N2 for three days, then cooled to 0°. The crystalline solid was broken up, filtered off, washed with toluene and with ether, and then dissolved in a minimum of CH2Cl2. This solution was diluted with stirring to 4 L with ether, the white crystalline powder was filtered off and dried at 40°/1 ml; 524 g (87%), mp 95-98° . Calculated for C29H36 BrO2P: C, 66.03; H, 6.88. Found: C,66.36; H, 6.95.

Workup

  1. temperaturerefluxed under N2 for three days
  2. temperaturecooled to 0°
  3. filtrationfiltered off
  4. washwashed with toluene and with ether
  5. dissolutiondissolved in a minimum of CH2Cl2
  6. additionThis solution was diluted
  7. filtrationthe white crystalline powder was filtered off
  8. customdried at 40°/1 ml

Sources & evidence

ORD record
ord-20df7676ce50405281a027abb8e674f4
Source dataset
uspto-grants-1991_10
Patent number
US05055613

Reaction notes

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