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

HRID 277345

Reaction equation

HRID 277345 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Cl:14])=[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.CCOCC>C1(C)C=CC=CC=1>[Cl-:14].[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][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

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 383834[4-(Benzyloxy)benzyl](triphenyl)phosphonium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Benzyloxybenzyl chloride (1 g, 0.0043 mol) and triphenyl phosphine (1.127 g, 1 equivalent) in anhydrous toluene (20 mL) were refluxed under nitrogen for ˜8-10 hours. A white precipitate appeared in the reaction mixture. The reaction mixture was then cooled to room temperature and ether (100 mL) was added. The precipitated phosphonium salt was collected by filtration, rinsed with ether and air dried. Yield=0.55 g (25%). MALDI-TOF MS 459.51 obs. (459.54 calc.).

Workup

  1. filtrationThe precipitated phosphonium salt was collected by filtration
  2. washrinsed with ether and air
  3. customdried

Sources & evidence

ORD record
ord-5fec410a09354eb1a80b0b1332618c8c
Source dataset
uspto-grants-2002_03
Patent number
US06355803B1

Linked notes

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