Triphenylphosphine → (6-Chloro-2-oxohexyl) triphenylphosphonium chloride

HRID 616776Notes

Reaction equation

HRID 616776 reaction equation
[Cl:1][CH2:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][Cl:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[Cl-:1].[Cl:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3](=[O:9])[CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 128060181,6-Dichlorohexan-2-one

Product 1

HCID 20526427(6-Chloro-2-oxohexyl) triphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 41 parts of 1,6-dichloro-2-hexanone in 400 parts by volume of benzene is added 44 parts of triphenylphosphine and the resulting solution is stored, in the absence of light for about 6 days, at the end of which time the crude product has crystallized from the mixture. That material is collected by filtration and is purified by recrystallization from acetone to afford (6-chloro-2-oxohexyl)triphenylphosphonium chloride. This product melts at 158°-161° C. and is characterized by 60-MHz nuclear magnetic resonance peaks in CDCl3 (deuterated chloroform) at 100 cps (multiplet), 140 cps (multiplet), 180 cps (multiplet), 208 cps (multiplet) and 357 cps (doublet, J≃12) in addition to the aromatic protons. The C1 protons at 375 cps exchange with D2O (deuterated water).

Workup

  1. customthe crude product has crystallized from the mixture
  2. filtrationThat material is collected by filtration
  3. customis purified by recrystallization from acetone

Sources & evidence

ORD record
ord-8815ec5d4421419789eff2f0573ce493
Source dataset
uspto-grants-1978_02
Patent number
US04075407

Reaction notes

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