반응 #65578

반응 방정식

water

methyl 3-cyclododecylpropanoate

sodium hydroxide

→

title compound

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

용매

methanol

반응 조건

후처리

1. 1
   온도is maintained for 4 hours
2. 2
   추출is extracted with hexane
3. 3
   추출is extracted (2 times) with ethyl ether
4. 4
   세척The combined ethereal extracts are washed with 1N hydrochloric acid
5. 5
   건조are dried over magnesium sulfate
6. 6
   여과Filtration and evaporation
7. 7
   기타gives 7.48 g of crude title compound
8. 8
   기타Recrystallization of a portion of the product from hexane

실험 절차

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.

출처