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

HRID 2164358Notes

Reaction equation

HRID 2164358 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

(B.) 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-7e7e18dd8c66408994898d44addb137e
Source dataset
uspto-grants-1985_03
Patent number
US04504304

Reaction notes

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