Benzene → Phenoxyacetylmethyltriphenylphosphonium Chloride

HRID 2199030Notes

Reaction equation

HRID 2199030 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-10c4aa3e386641168dec94f2a230de63
Source dataset
uspto-grants-1982_11
Patent number
US04361514

Reaction notes

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