Chloroform → Acetonyltriphenylphosphonium chloride

HRID 223763Notes

Reaction equation

HRID 223763 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:20][CH2:21][C:22](=[O:24])[CH3:23].C(Cl)(Cl)Cl>CCOCC>[Cl-:20].[CH2:21]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:22]([CH3:23])=[O:24]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6571ChloroacetoneHCID 11776Triphenylphosphine

Product 1

HCID 196994Acetonyltriphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 55 g of triphenylphosphine, 15.5 ml of chloroacetone and 165 ml of chloroform was refluxed for 45 minutes and after cooling to 20° C., the mixture was poured into 1.65 liters of ether. The mixture was vacuum filtered and the recovered product was washed with ether and dried under reduced pressure to obtain 26.9 g of acetonyltriphenylphosphonium chloride. The said product was added to 270 ml of aqueous 10% sodium carbonate solution and the mixture was stirred for 16 hours and was vacuum filtered. The product was washed with water and dried under reduced pressure to obtain 20.3 g of raw product which was crystallized from 50% aqueous methanol to obtain 16 g of acetonylidene triphenylphosphorane melting at 207°-208° C.

Workup

  1. filtrationfiltered
  2. washthe recovered product was washed with ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-8e618eb724d1409b86bb458327ec9823
Source dataset
uspto-grants-1982_10
Patent number
US04356187

Reaction notes

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