تفاعل #65578

معادلة التفاعل

water

methyl 3-cyclododecylpropanoate

sodium hydroxide

→

title compound

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

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis maintained for 4 hours
2. 2
   استخلاصis extracted with hexane
3. 3
   استخلاصis extracted (2 times) with ethyl ether
4. 4
   غسيلThe combined ethereal extracts are washed with 1N hydrochloric acid
5. 5
   تجفيفare dried over magnesium sulfate
6. 6
   ترشيحFiltration and evaporation
7. 7
   أخرىgives 7.48 g of crude title compound
8. 8
   أخرىRecrystallization of a portion of the product from hexane

الإجراء التجريبي

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.

المصدر