Diethyl Ether → Phenoxyacetylmethyltriphenylphosphonium Chloride

HRID 2052338Notes

Reaction equation

HRID 2052338 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)C>C(Cl)(Cl)Cl>[Cl-:1].[O:4]=[C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 116224561-Chloro-3-phenoxypropan-2-one

Product 1

HCID 20516787Phenoxyacetylmethyltriphenylphosphonium ChlorideYield 62.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-chloro-3-phenoxyacetone (6.8 g.) and triphenylphosphine (12 g.) in chloroform (16 ml.) was saturated with nitrogen and heated at reflux under nitrogen overnight. An excess of dry diethyl ether was added, and then the solvents were decanted from the gum that separated. The remaining solvent was removed in vacuo to give crude 2-oxo-3-phenoxypropyltriphenylphosphonium chloride (10.35 g.). This was stirred vigorously with a solution of sodium carbonate (18 g.) in water (180 ml.) for 24 hours. The solution was extracted with diethyl ether and the ethereal extracts dried over sodium sulphate. The solvent was removed by evaporation to give phenoxyacetylmethylenetriphenylphosphorane (5.3 g.), a sticky solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen overnight
  3. customthe solvents were decanted from the gum
  4. customthat separated
  5. customThe remaining solvent was removed in vacuo

Sources & evidence

ORD record
ord-834ddb0d070947479a6f7804eedcbcdc
Source dataset
uspto-grants-1980_01
Patent number
US04183870

Reaction notes

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