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

HRID 280066Notes

Reaction equation

HRID 280066 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-Isopropylbenzylchoride (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-3f5d930eeefa4cee96ee58a8f88c7521
Source dataset
uspto-grants-1986_05
Patent number
USRE032147

Reaction notes

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