Acetic Acid → 2-(Propan-2-ylidene)cyclopentan-1-one

HRID 1198633Notes

Reaction equation

HRID 1198633 reaction equation
[CH3:1][C:2]([CH3:4])=O.[OH-].[Na+].[C:7]1(=[O:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(O)(=O)C>O>[CH3:1][C:2](=[C:8]1[CH2:9][CH2:10][CH2:11][C:7]1=[O:12])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 8452CyclopentanoneHCID 14798Sodium Hydroxide

Product 1

HCID 53240552-(Propan-2-ylidene)cyclopentan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 190 ml of acetone and 36.0 g of sodium hydroxide in 600 ml of water was treated with 60.0 g of cyclopentanone under stirring. After stirring for about 12 hours at about room temperature, the mixture was neutralized with 36% acetic acid and extracted with three 60 ml portions of ether. The combined extracts were dried over anhydrous magnesium sulfate and evaporated to give a residue. The residue was distilled to obtain 62.6 g of 2-(1-methylethylidene) cyclopentanone as a colorless liquid. The boiling point of this intermediate compound was determined to be 85°-88° C. at a pressure of 10 mm Hg. A subsequent Mannich reaction yielded the 2-Dimethylaminomethyl-5-(1-methylethylidene) cyclopentanone hydrochloride. The melting point of the product was determined to be 173°-175° C.

Workup

  1. stirringAfter stirring for about 12 hours at about room temperature
  2. extractionextracted with three 60 ml portions of ether
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto give a residue
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-a5c60abb0cd941c8be4657dcfab835bc
Source dataset
uspto-grants-1994_01
Patent number
US05281622

Reaction notes

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