Triphenylphosphine → 3-Phenoxyphenylmethyltriphenylphosphonium chloride

HRID 1383227Notes

Reaction equation

HRID 1383227 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][Cl:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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>C1(C)C=CC=CC=1>[Cl-:15].[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][P+:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 932913-Phenoxybenzyl chloride

Product 1

HCID 212741653-Phenoxyphenylmethyltriphenylphosphonium chlorideYield 44.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 5.0 grams (0.0228 mole) of 3-phenoxyphenylmethyl chloride and 5.6 grams (0.0217 mole) of triphenyl phosphine in 50 mL of dry toluene was heated at reflux for 8 hours. The reaction mixture was cooled and filtered to collect a solid. The solid was washed with pentane and dried, yielding 4.6 grams of 3-phenoxyphenylmethyltriphenylphosphonium chloride. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto collect a solid
  5. washThe solid was washed with pentane
  6. customdried

Sources & evidence

ORD record
ord-4683012408c8434382ea69834cd388e0
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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