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

HRID 1465482

Reaction equation

HRID 1465482 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][Cl:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl-:16].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][P+:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 383834[4-(Benzyloxy)benzyl](triphenyl)phosphonium chlorideYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 1-(benzyloxy)-4-(chloromethyl)benzene (4.890 g, 21.01 mmol) in toluene (25 ml) was added triphenylphosphine (6.617 g, 25.23 mmol). The mixture was heated under reflux for 24 hrs, and cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give [4-(benzyloxy)benzyl](triphenyl)phosphonium chloride (9.166 g, yield 88.1%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hrs
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-813e6d3b514547329678200b2299595c
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Linked notes

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