2-Methylcyclopentanone → 2-Methyl-5-(4-methoxybenzylidene)-cyclopentanone

HRID 1599794Notes

Reaction equation

HRID 1599794 reaction equation
[OH-].[K+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[CH:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>O>[CH3:3][CH:4]1[CH2:8][CH2:7][C:6](=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:5]1=[O:9]

Participants

5

Reactant 3

HCID 142652-MethylcyclopentanoneHCID 14797Potassium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 537645382-Methyl-5-(4-methoxybenzylidene)-cyclopentanoneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2.8 g of 85% strength aqueous potassium hydroxide solution and 250 ml of water was charged to a 0.71 stainless-steel autoclave, and 49 g of 2-methylcyclopentanone and 68 g of p-anisaldehyde were added. The mixture was subsequently heated to 120° C. with stirring under the intrinsic pressure and subsequently stirred under the intrinsic pressure (1.5 bar) for 3 hours. After cooling to room temperature, the precipitated solid was filtered off with suction, washed to neutrality with water and dried in a vacuum oven at 55° C. In this way 101.5 g of 2-methyl-5-(4-methoxybenzylidene)-cyclopentanone (pure according to gas chromatography) were obtained. This corresponds to a yield of 94% of theory.

Workup

  1. additionwere added
  2. stirringsubsequently stirred under the intrinsic pressure (1.5 bar) for 3 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe precipitated solid was filtered off with suction
  5. washwashed
  6. customdried in a vacuum oven at 55° C

Sources & evidence

ORD record
ord-4c4f2382d18e480a945be9e56757d5b1
Source dataset
uspto-grants-1998_04
Patent number
US05741937

Reaction notes

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