Chloroform → 4-Phenylbutanoylmethyltriphenylphosphonium chloride

HRID 372067Notes

Reaction equation

HRID 372067 reaction equation
[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14]1([P:20]([C:27]2C=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:33](Cl)(Cl)Cl>>[Cl-:1].[C:7]1([CH2:6][CH2:5][CH2:4][C:3]([C:2]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[P+:20]([CH3:33])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 11776TriphenylphosphineHCID 125176971-Chloro-5-phenylpentan-2-one

Product 1

HCID 867357054-Phenylbutanoylmethyltriphenylphosphonium chloride

Procedure

A solution of 1-chloro-2-oxo-5-phenylpentane (6.55 g.) in dry chloroform (30 ml.) was added to a solution of triphenylphosphine (8.7 g.) in dry chloroform (30 ml.) and heated at reflux in an atmosphere of dry nitrogen for 4 hours. The solution was then evaporated under reduced pressure and the residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether, to give a white solid. Recrystallisation of this material from a mixture of dichloromethane and diethyl ether gave 4-phenylbutanoylmethyltriphenylphosphonium chloride (11.2 g.) in the form of a white crystalline solid. m.p. 192-195° C. (Elemental analysis: C, 76.0; H, 6.2%; C29H28ClOP requires: C, 75.9; H, 6.2%; νmax 1110 cm-1, 1445 cm-1, 1490 cm-1, 1695 cm-1).

Workup

  1. temperatureheated
  2. temperatureat reflux in an atmosphere of dry nitrogen for 4 hours
  3. customThe solution was then evaporated under reduced pressure
  4. customthe residual oil was triturated with a mixture of light petroleum ether (b.p. 40°-60° C.) and diethyl ether
  5. customto give a white solid
  6. customRecrystallisation of this material
  7. additionfrom a mixture of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-fe8e53098cce4cb08714b39b96f74b62
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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