Triphenylphosphine → 2-Heptanone, 1-(triphenylphosphoranylidene)-

HRID 1581093Notes

Reaction equation

HRID 1581093 reaction equation
Cl[CH2:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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>C(Cl)(Cl)Cl>[C:3]([CH: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)(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 109536781-Chloroheptan-2-one

Product 1

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-Yield 20.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-chloro-2-heptanone (33 g.) and triphenylphosphine (60 g.) in chloroform (50 ml.) was saturated with nitrogen and refluxed under nitrogen overnight. The chloroform was removed in vacuo and the residue was dissolved in methylene chloride (150 ml.). Dry diethyl ether (600 ml.) was added to precipitate 2-oxoheptyltriphenylphosphonium chloride (60 g.), m.p. 165°-168°C. This compound (23 g.) was added portionwise to a solution of sodium carbonate (25 g.) in water (250 ml.), and the mixture was stirred vigorously for 24 hours. The solution was extracted with diethyl ether, and the ethereal extracts were dried over magnesium sulphate. The solvent was removed by evaporation and the residue was cooled and triturated with petrol (b.p. 40°-60°C.). The solid thus obtained was recrystallised from petrol (b.p. 60°-80°C.) to give hexanoylmethylene triphenylphosphorane (17 g.), m.p. 73°-74°C.

Workup

  1. temperaturerefluxed under nitrogen overnight
  2. customThe chloroform was removed in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride (150 ml.)
  4. additionDry diethyl ether (600 ml.) was added to precipitate 2-oxoheptyltriphenylphosphonium chloride (60 g.), m.p. 165°-168°C
  5. additionThis compound (23 g.) was added portionwise to a solution of sodium carbonate (25 g.) in water (250 ml.)
  6. extractionThe solution was extracted with diethyl ether
  7. dry with materialthe ethereal extracts were dried over magnesium sulphate
  8. customThe solvent was removed by evaporation
  9. temperaturethe residue was cooled
  10. customtriturated with petrol (b.p. 40°-60°C.)
  11. customThe solid thus obtained
  12. customwas recrystallised from petrol (b.p. 60°-80°C.)

Sources & evidence

ORD record
ord-b4da4390dbfe4d0391db24200d660886
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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