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

HRID 1431912Notes

Reaction equation

HRID 1431912 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 moles) 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-e565d9f02d4240609cdd5106b7ef50da
Source dataset
uspto-grants-2009_11
Patent number
US07611909B1

Reaction notes

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