Реакция #65578

Уравнение реакции

water

methyl 3-cyclododecylpropanoate

sodium hydroxide

→

title compound

3-(3-Cyclododecyl-1-oxopropyl)-4-hydroxy-2(5H)-furanone

Растворители

methanol

Условия реакции

Обработка

1. 1
   Температураis maintained for 4 hours
2. 2
   Экстракцияis extracted with hexane
3. 3
   Экстракцияis extracted (2 times) with ethyl ether
4. 4
   ПромывкаThe combined ethereal extracts are washed with 1N hydrochloric acid
5. 5
   Сушкаare dried over magnesium sulfate
6. 6
   ФильтрацияFiltration and evaporation
7. 7
   Другоеgives 7.48 g of crude title compound
8. 8
   ДругоеRecrystallization of a portion of the product from hexane

Методика

To a solution of 7.6 g (30 mmol) of methyl 3-cyclododecylpropanoate in 100 ml of methanol is added 2.4 g of sodium hydroxide. The mixture is heated to 55° C. and is maintained for 4 hours. The reaction mixture is diluted with water and is extracted with hexane. The aqueous phase is acidified with 1N hydrochloric acid and is extracted (2 times) with ethyl ether. The combined ethereal extracts are washed with 1N hydrochloric acid and are dried over magnesium sulfate. Filtration and evaporation gives 7.48 g of crude title compound. Recrystallization of a portion of the product from hexane gives 1.81 g of the title compound: m.p. 72°-74° C.; IR (KBr) 1715 cm-1 ; NMR (CDCl3) δ 1.34 (m, 23H), 1.57 (q, 2H, J=8 Hz), 2.36 (t, 2H, J=8 Hz). Anal. Calc'd. for C15H28O2 : C, 74.95;H, 11.74; Found: C, 74.90;H, 11.20.

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