Toluene → Ethyl 1-(7-ethoxy-7-oxoheptyl)-2-oxocyclopentane-1-carboxylate

HRID 1580338Notes

Reaction equation

HRID 1580338 reaction equation
[K].[CH3:2][CH2:3][O:4][C:5]([CH:7]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8]1)=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].[C:23]1(C)C=CC=C[CH:24]=1>>[C:5]([C:7]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:8][CH2:9][CH2:10][C:11]1=[O:12])([O:4][CH2:3][CH3:2])=[O:6]

Participants

5

Reactant 4

HCID 1140TolueneHCID 69136Ethyl 2-oxocyclopentanecarboxylate2×HCID 1217237-Bromoheptanoic acidHCID 5462222Potassium2×

Product 1

HCID 13046295Ethyl 1-(7-ethoxy-7-oxoheptyl)-2-oxocyclopentane-1-carboxylate

Procedure

Under agitation, 500 g. of potassium salt of the ethyl ester of 2-oxocyclopentanecarboxylic acid is added to a boiling solution of 550 g. of the ethyl ester of 7-bromoenanthic acid in 6 l. of toluene; the mixture is further refluxed and, after one hour, another 250 g. of the potassium salt of the ethyl ester of 2-oxocyclopentanecarboxylic acid is added thereto. The reaction mixture is refluxed for another 24 hours, filtered after cooling, the solvent is distilled off, the residue is diluted with 3 l. of ether, washed with water, dried over Na2SO4, and the solvent is distilled off. After fractionation of the residue, 2-carbethoxy-2-(6-carbethoxyhexyl)-cyclopentanone is obtained as a colorless oil, b.p. = 165° (0.3 mm. Hg).

Workup

  1. temperaturethe mixture is further refluxed and, after one hour
  2. temperatureThe reaction mixture is refluxed for another 24 hours
  3. filtrationfiltered
  4. temperatureafter cooling
  5. distillationthe solvent is distilled off
  6. additionthe residue is diluted with 3 l
  7. washof ether, washed with water
  8. dry with materialdried over Na2SO4
  9. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-c9a3c1767ee54421862774dd4534d6a2
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

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