1-Chloro-4-(chloromethyl)benzene → (4-Chlorobenzyl)triphenylphosphonium chloride

HRID 1106040Notes

Reaction equation

HRID 1106040 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>C1(C)C(C)=CC=CC=1>[Cl-:20].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11776Triphenylphosphine

Product 1

HCID 2733546(4-Chlorobenzyl)triphenylphosphonium chlorideYield 126.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution of 158 g, (0.6 mole) of triphenylphosphine in 800 ml of xylene is treated with 97 g of 4-chlorobenzyl chloride. The resulting solution is heated (product begins to crystallize at this point) and refluxed for six hours. After standing overnight at room temperature, the solid is filtered, washed with xylene and then with ethyl acetate, and dried in a desiccator to yield 161 g of colorless solid [(4-chlorophenyl)methyl]triphenylphosphonium chloride; m.p. 283°-285°.

Workup

  1. temperatureThe resulting solution is heated (product
  2. customto crystallize at this point) and
  3. temperaturerefluxed for six hours
  4. filtrationthe solid is filtered
  5. washwashed with xylene
  6. dry with materialwith ethyl acetate, and dried in a desiccator

Sources & evidence

ORD record
ord-f2a25579520f4f199dd3dce3e4ac157b
Source dataset
uspto-grants-1982_01
Patent number
US04311705

Reaction notes

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