Benzene → Cyclopentanecarboxylic acid, 2-oxo-1-(3-oxobutyl)-, ethyl ester

HRID 371186Notes

Reaction equation

HRID 371186 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C=CC=CC=1.[CH:18]([C:20]([CH3:22])=[O:21])=[CH2:19]>C(N(CC)CC)C>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C:3]1([CH2:19][CH2:18][C:20](=[O:21])[CH3:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6570Methyl vinyl ketoneHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 11806371Cyclopentanecarboxylic acid, 2-oxo-1-(3-oxobutyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 102.0 g of ethyl 2-oxocyclopentanecarboxylate, 300 ml of benzene, 67 ml of methyl vinyl ketone and 20 ml of triethylamine was allowed to stir magnetically at reflux for 2.5 hours. Concentration followed by Claisen distillation gave 128 g of product.

Workup

  1. temperatureat reflux for 2.5 hours
  2. concentrationConcentration
  3. distillationfollowed by Claisen distillation

Sources & evidence

ORD record
ord-77703c370b164b45b7970abd384ad3c4
Source dataset
uspto-grants-1985_07
Patent number
US04529806

Reaction notes

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