Triphenylphosphine → (2-Chloro-6-methylbenzyl)(triphenyl)phosphonium chloride

HRID 1667300Notes

Reaction equation

HRID 1667300 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8]O.[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.C1(C)C=CC=CC=1.C(#N)C>[Cl-:3].[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=1[CH2:8][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 20579023(2-Chloro-6-methylphenyl)methanol

Product 1

HCID 86612298(2-Chloro-6-methylbenzyl)(triphenyl)phosphonium chloride

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

Under ice cooling, 5 drops of dimethylformamide and 0.75 ml of thionyl chloride were added to a solution of 1.24 g of 2-chloro-6-methylbenzyl alcohol in 15 ml of toluene. The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was then azeotropically distilled with 5 ml of toluene 3 times to give an oil. The resulting oil was dissolved in 15 ml of acetonitrile, and 2.08 g of triphenylphosphine was added to the solution. The mixture was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure and the collected crystals were washed with ethyl acetate to give 3.15 g of (2-chloro-6-methylbenzyl)(triphenyl)phosphonium chloride as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationthe residue was then azeotropically distilled with 5 ml of toluene 3 times
  3. customto give an oil
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 16 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. washthe collected crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-a5f273a9a9b74e108b4c33fbcdd0f952
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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