Hydrochloric Acid → Methyl 3-(4-chlorobenzylidene)-1-methyl-2-oxocylopentanecarboxylate

HRID 440566Notes

Reaction equation

HRID 440566 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.Cl>O.CO>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:6]2[CH2:7][CH2:8][C:4]([CH3:3])([C:10]([O:12][CH3:13])=[O:11])[C:5]2=[O:9])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 121785Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl ester

Product 1

HCID 67742476Methyl 3-(4-chlorobenzylidene)-1-methyl-2-oxocylopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.4 g of sodium hydroxide in 770 ml of water were added 15 g of methyl 1-methyl-2-oxocylopentanecarboxylate (prepared in Reference Example 1 hereinafter) and a solution of 13.5 g of 4-chlorobenzaldehyde in 800 ml of methanol, and the mixture was stirred for 5 hours at room temperature. The reaction mixture was neutralized with diluted hydrochloric acid and the solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed with water and dried. Ethyl acetate was evaporated under reduced pressure to obtain 25 g of an oily matter.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customEthyl acetate was evaporated under reduced pressure
  6. customto obtain 25 g of an oily matter

Sources & evidence

ORD record
ord-c761f163fbaf469d9b12f80f4750cf53
Source dataset
uspto-grants-1996_05
Patent number
US05519160

Reaction notes

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