Acetic Acid → HCID 22709050, compound

HRID 352278Notes

Reaction equation

HRID 352278 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]([C:10]([CH3:12])=[O:11])=[CH2:9].[C:13]([O-])(=O)[CH3:14].[Na+].C(O)(=O)C>O>[CH2:7]([CH:1]1[CH2:6][CH2:5][C:4]2[CH:3]([CH2:9][CH2:8][C:10](=[O:11])[CH:12]=2)[CH2:2]1)[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 6570Methyl vinyl ketoneHCID 517045Sodium Acetate

Product 1

HCID 22709050HCID 22709050, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

212 g of 4-propylcyclohexanone and 200 ml of pyrrolidine was dissolved in 600 ml of toluene, and the mixture was heated with stirring for 3 hours, and any azeotropically distilled water was removed. Excess pyrrolidine was then removed by azeotropic distillation with toluene, to obtain 1-(4-propylcyclohexa-1-en-1-yl)-pyrrolidine. The crude product was cooled, as is, to room temperature, a further 800 ml of toluene was added, the mixture was cooled in a water bath, and 120 ml of methyl vinyl ketone was added dropwise over a period of 1 hour at a temperature of 25° C. or lower. Following completion of the addition, the mixture was immediately heated and refluxed for 20 hours. The solution was then cooled to room temperature, a buffer solution of pH 5 prepared from 63 g of sodium acetate, 120 ml of acetic acid and 140 ml of water was added, and the reflux was continued for a further 4 hours. After the solution had been cooled to room temperature, the organic layer was separated and washed with water and a saturated aqueous solution of sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, and the solvent removed by evaporation to obtain 320 g of a crude product of 6-propyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one.

Workup

  1. customas is, to room temperature
  2. temperaturethe mixture was cooled in a water bath
  3. additioncompletion of the addition
  4. temperaturethe mixture was immediately heated
  5. temperaturerefluxed for 20 hours
  6. additionwas added
  7. temperatureAfter the solution had been cooled to room temperature
  8. customthe organic layer was separated
  9. washwashed with water
  10. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  11. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-d5223ae41b35441b97f00f1dd35044b1
Source dataset
uspto-grants-2004_06
Patent number
US06746728B1

Reaction notes

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