Water → 4-(2-(4-n-Propylphenyl)ethenyl)cyclohexanone

HRID 342353Notes

Reaction equation

HRID 342353 reaction equation
[Br-].[CH2:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)[CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH:37]([CH:39]1[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]1)=O.O>C1COCC1>[CH2:2]([C:5]1[CH:30]=[CH:29][C:8]([CH:9]=[CH:37][CH:39]2[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]2)=[CH:7][CH:6]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 111709734-Oxocyclohexane-1-carbaldehydeHCID 231188394-n-Propylbenzyltriphenyl phosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 539175704-(2-(4-n-Propylphenyl)ethenyl)cyclohexanoneYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Suspension of 114 g of 4-n-propylbenzyltriphenyl phosphonium bromide in 500 ml of THF was stirred under nitrogen gas stream and 32.3 g of potassium-t-butoxide was added thereto at room temperature. After stirred at room temperature for 1 hour, a solution of 31.2 g of 4-formylcyclohexanone in 200 ml of THF was added dropwise to the suspension. After stirred at room temperature for 2 hours, 1 l of water was added thereto and then it was extracted with 1 l of ethyl acetate. Organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and then 500 ml of heptane was added thereto. Precipitate thus separated was filtered off and purified by a column chromatography over a silica gel by using ethyl acetate/heptane (1/5) as an eluent, and the solvent was distilled off under a reduced pressure to obtain 42 g of 4-(2-(4-n-propylphenyl)ethenyl)cyclohexanone.

Workup

  1. additionwas added
  2. customat room temperature
  3. stirringAfter stirred at room temperature for 2 hours
  4. extractionit was extracted with 1 l of ethyl acetate
  5. washOrganic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under a reduced pressure
  8. addition500 ml of heptane was added
  9. customPrecipitate thus separated
  10. filtrationwas filtered off
  11. custompurified by a column chromatography over a silica gel
  12. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-33b5b69282e94b6a9042cc103cecc836
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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