Triphenylphosphine → 3-Methyl-4-methoxybenzyl triphenylphosphonium chloride

HRID 270156

Reaction equation

HRID 270156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Cl:10])=[CH:5][C:4]=1[CH3:11].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Cl-:10].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][P+:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1437424-Methoxy-3-methylbenzyl chloride

Product 1

HCID 461800353-Methyl-4-methoxybenzyl triphenylphosphonium chlorideYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 250ml round-bottom flask equipped with a magnetic stir-bar and N2inlet was added 4-(Chloromethyl)-2-methylphenyl methyl ether (2.59g, 15.18mmoles, 1eq), dry toluene (50ml, 0.3M) and triphenylphosphine (3.98g, 15.18mmoles, 1eq). The reaction mixture was refluxed overnight. After cooling to room temperature the solvent was removed in vacuo, the residue washed with hexanes and the solid/liquid mixture was filtered to yield 4.48g (71%) of solid product.

Workup

  1. customTo a 250ml round-bottom flask equipped with a magnetic stir-bar
  2. temperatureThe reaction mixture was refluxed overnight
  3. customwas removed in vacuo
  4. washthe residue washed with hexanes
  5. filtrationthe solid/liquid mixture was filtered

Sources & evidence

ORD record
ord-a8fd80fb3ecd46b39c18bdf4df3422d0
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Linked notes

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