Triphenylphosphine → (4-Methoxybenzyl)triphenylphosphonium chloride

HRID 6605

Reaction equation

HRID 6605 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[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.CCOCC>[Cl-:8].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][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:5][CH:4]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 2773651(4-Methoxybenzyl)triphenylphosphonium chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-methoxybenzyl chloride (1.153 g, 0.0074 mol) in anhydrous toluene (10 mL) was treated with triphenylphosphine (1.93 g, 1 equivalent). The resulting solution was refluxed under nitrogen. After 8–10 hours, the reaction was cooled to room temperature and diluted with ether. The phosphonium salt was collected by filtration. Yield=1.5 g (53%); MALDI-TOF MS 383.9 obs. (383.45 calc.).

Workup

  1. temperatureThe resulting solution was refluxed under nitrogen
  2. waitAfter 8–10 hours
  3. filtrationThe phosphonium salt was collected by filtration

Sources & evidence

ORD record
ord-22369baf791041d692ac21ca9695965b
Source dataset
uspto-grants-2006_08
Patent number
US07083986B2

Linked notes

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