Реакция #656405

Уравнение реакции

sodium bicarbonate

3-(5-ethoxyheptyl)cyclopentene

trichloroacetyl chloride

phosphorous oxychloride

→

7,7-dichloro-4-(5-ethoxyheptyl)bicyclo [3.2.0]heptan 6-one

Растворители

ether

ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONis added dropwise to a reaction vessel
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Температураis refluxed for 4 hours
4. 4
   ФильтрацияThe solution is filtered
5. 5
   Другоеthe phases separated
6. 6
   Экстракцияthe aqueous layer is extracted with ether
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   ДругоеThe solvent is removed under vacuum
9. 9
   Другоеleaving a clear yellow oil
10. 10
    workup.DISTILLATIONThe crude product is fractionally distilled under vacuum

Методика

A solution containing trichloroacetyl chloride (187 g, 1.03 moles) and phosphorous oxychloride (158 g, 1.03 moles), both dissolved in 500 ml ether (1700 ml) is added dropwise to a reaction vessel containing zinc/copper couple (75 g, 1.15 moles), 3-(5-ethoxyheptyl)cyclopentene (170 g, 0.573 moles), and ether (1700 ml). After the addition is complete the reaction is refluxed for 4 hours. The reaction vessel is cooled to room temperature and the mixture neutralized by adding it to a saturated solution of sodium bicarbonate. The solution is filtered, the phases separated, and the aqueous layer is extracted with ether. The organic phases are combined and dried over anhydrous sodium sulfate. The solvent is removed under vacuum leaving a clear yellow oil. The crude product is fractionally distilled under vacuum leaving the product as a clear, colorless oil of 7,7-dichloro-4-(5-ethoxyheptyl)bicyclo [3.2.0]heptan 6-one, BP 145° C./0.3 mm.

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