Benzene → Phenoxyacetylmethyltriphenylphosphonium Chloride

HRID 613978Notes

Reaction equation

HRID 613978 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.C1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl-:1].[O:6]([CH2:5][C:3]([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)=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 11776TriphenylphosphineHCID 116224561-Chloro-3-phenoxypropan-2-one

Product 1

HCID 20516787Phenoxyacetylmethyltriphenylphosphonium Chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-Chloro-3-phenoxyacetone (13 g, 0.07 mole) dissolved in 20 ml chloroform was mixed with a solution of triphenylphosphine (19.7 g, 1 eq) in 30 ml chloroform at room temperature. The mixture was swirled for 5 minutes and benzene (20 ml) was added. A white crystalline compound appeared when most of the solvents had been evaporated. The product was collected by suction and washed with benzene. Second and third crops were collected by evaporation of the washings. The total yield was 23 g (73%); sublimation without melting at 90°; ir (KBr, cm-1) 3450-3280, 2770, 1720, 1595, 1585, 1485, 1435, 1220, 1110, 1030; nmr (DCCl3, ppm) 8.20-6.80 (m, 22H), 5.30 (br, 2H).

Workup

  1. customhad been evaporated
  2. customThe product was collected by suction
  3. washwashed with benzene
  4. customSecond and third crops were collected by evaporation of the washings

Sources & evidence

ORD record
ord-ea09d7deb935474b82810f7e4cee1f09
Source dataset
uspto-grants-1979_03
Patent number
US04143046

Reaction notes

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