Reaktion #219963

Reaktionsgleichung

ethyl 1-ethyl-2-hydroxy-cyclopentane carboxylate

acetic anhydride

→

colorless liquid

Ethyl 1-ethyl-2-acetoxy-cyclopentane carboxylate

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react
2. 2
   Temperaturunder reflux condition for 2 hours
3. 3
   WaschenThe reaction mixture was washed with 50 ml of ethyl acetate and 50 ml of water, and organic layer
4. 4
   Sonstigewas separated
5. 5
   WaschenThen the organic layer was washed with 10% aqueous solution of sodium carbonate twice
6. 6
   Trocknenwith saline solution to neutrality, and dried over anhydrous magnesium sulfate

Vorschrift

5.58 grams of ethyl 1-ethyl-2-hydroxy-cyclopentane carboxylate obtained in Example 15 was diluted with 50 ml of methylene chloride. To the solution were added several drops of concentrated sulfuric acid, then dropwise added 4.32 ml of acetic anhydride. The mixture was allowed to react under reflux condition for 2 hours. The reaction mixture was washed with 50 ml of ethyl acetate and 50 ml of water, and organic layer was separated. Then the organic layer was washed with 10% aqueous solution of sodium carbonate twice, then with saline solution to neutrality, and dried over anhydrous magnesium sulfate. Removing solvent gave 5.91 g of colorless liquid. Yield after chromatography purification: 83.20%. MS: m/e 228(M+′), 183(M+—OCH2CH3), 169 (M+—CH3CO2), 158, 155, 140, 129, 113, 101.

Quelle