Triphenylphosphine → 2-Methoxymethoxybenzyltriphenylphosphonium chloride

HRID 743381Notes

Reaction equation

HRID 743381 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.[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][Cl:27]>C1(C)C=CC=CC=1>[Cl-:27].[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 22345410HCID 22345410, compound

Product 1

HCID 194239962-Methoxymethoxybenzyltriphenylphosphonium chlorideYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

32 g of triphenylphosphine were added to a solution of 15.0 g of 2-methoxymethoxybenzyl chloride [prepared as described in step (a) above] in 150 ml of toluene, and the resulting mixture was heated under reflux for 14 hours. At the end of this time, the reaction mixture was cooled, and the resulting precipitates were collected by filtration, washed with toluene and dried in vacuo, to give 21.3 g (yield 59%) of the title compound as a colorless solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with toluene
  7. customdried in vacuo

Sources & evidence

ORD record
ord-064745d8cce245f49bf771826eaa4cd6
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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