Triphenylphosphine → [4-(Hydroxymethyl)benzyl](triphenyl)phosphonium chloride

HRID 1465470Notes

Reaction equation

HRID 1465470 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Cl-:1].[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][P+:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 23447282[4-(Hydroxymethyl)benzyl](triphenyl)phosphonium chlorideYield 91.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of [4-(chloromethyl)phenyl]methanol (4.691 g, 29.96 mmol) in toluene (30 ml) was added triphenylphosphine (9.444 g, 36.01 mmol). The mixture was heated under reflux for 20 hrs, and cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give [4-(hydroxymethyl)benzyl](triphenyl)phosphonium chloride (11.47 g, yield 91.4%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 hrs
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-03c7c5dd2f614e53b36aa0039acbf192
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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