4-Chlorobenzaldehyde → 2-Methyl-5-(4-chlorobenzylidene)-cyclopentanone

HRID 1599792Notes

Reaction equation

HRID 1599792 reaction equation
[OH-].[K+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>O>[CH3:3][CH:4]1[CH2:8][CH2:7][C:6](=[CH:15][C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:5]1=[O:9]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 142652-MethylcyclopentanoneHCID 14797Potassium Hydroxide

Product 1

HCID 537529512-Methyl-5-(4-chlorobenzylidene)-cyclopentanoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 16.8 g of 85% strength aqueous potassium hydroxide solution and 1,500 ml of water was charged to a 31 stainless-steel autoclave, 294 g of 2-methylcyclopentanone and 421.8 g of 4-chlorobenzaldehyde were added, and the mixture was then heated to 120° C. under the intrinsic pressure. Stirring was subsequently carried out at this temperature for 3 hours. After cooling to room temperature, the finely particulate yellow product was filtered off with suction, washed to neutrality with water and then dried in a vacuum oven at 60° C. In this way 658.5 g of 2-methyl-5-(4-chlorobenzylidene)-cyclopentanone (93.1% pure) were obtained. This corresponds to a yield of 93% of theory.

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature
  3. filtrationthe finely particulate yellow product was filtered off with suction
  4. washwashed
  5. customdried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-b6401b97a28d4424875581dbe252bd8d
Source dataset
uspto-grants-1998_04
Patent number
US05741937

Reaction notes

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