Triphenylphosphine → Triphenyl{[4-(propan-2-yl)phenyl]methyl}phosphanium chloride

HRID 1414920Notes

Reaction equation

HRID 1414920 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Cl:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[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>[Cl-:9].[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][P+:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 749164-Isopropylbenzyl chloride

Product 1

HCID 23321400Triphenyl{[4-(propan-2-yl)phenyl]methyl}phosphanium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

p-Isopropylbenzylchloride (168.5 g, 1 mol.) and triphenylphosphine (275 g, 1.05 mol.) were refluxed overnight in acetonitrile (600 ml). Approximately 300 ml of acetonitrile were removed in vacuo and 500 ml ether was added. The salt was allowed to crystallize and the salt was filtered off and washed with ether. Yield of the first crop of crystals was 388 g (90%) of desired salt. Some additional salt could be recovered from the mother liquors.

Workup

  1. customApproximately 300 ml of acetonitrile were removed in vacuo and 500 ml ether
  2. additionwas added
  3. customto crystallize
  4. filtrationthe salt was filtered off
  5. washwashed with ether
  6. customSome additional salt could be recovered from the mother liquors

Sources & evidence

ORD record
ord-994591a66c6a4a1e82623a7af10762fa
Source dataset
uspto-grants-1977_01
Patent number
US04002769

Reaction notes

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