Toluene → ethyl 2-(1-methyl-2-oxocyclopentyl)acetate

HRID 1438921Notes

Reaction equation

HRID 1438921 reaction equation
C1(C)C=CC=CC=1.[CH3:8][CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C1C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][C:9]1([CH3:8])[CH2:13][CH2:12][CH2:11][C:10]1=[O:14])[CH3:21]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7748Ethyl bromoacetateHCID 142652-Methylcyclopentanone

Product 1

HCID 12292030ethyl 2-(1-methyl-2-oxocyclopentyl)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of sodium tert.-amylate in toluene (70 ml, 0.1 mole) is added dropwise with stirring under an atmosphere of nitrogen to a solution of 2-methylcyclopentanone (9.8 g, 0.1 mole) and ethyl bromoacetate (16.7 g, 0.1 mole) in dry benzene (100 ml). The reaction is exothermic, a precipitate is formed, and the mixture turns yellow-orange. Stirring is continued for 3 hrs. at room temperature, the solution is washed with 1% HCl, cold water, and brine, dried over anhydrous magnesium sulfate and the solvent evaporated to yield 1-methyl-2-oxocyclopentane acetic acid ethyl ester as a pale yellow oil which is used without further purification in the subsequent step and which is identical with the same compound described in Example 5.

Workup

  1. customa precipitate is formed
  2. washat room temperature, the solution is washed with 1% HCl, cold water, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-7a342331d404476e8fb65aada73f77cf
Source dataset
uspto-grants-1977_11
Patent number
US04057559

Reaction notes

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