反应 #1869152

反应方程式

ethyl 3-oxododecanoate

ethylene glycol

p-TsOH

→

ethyl 3,3-ethylenedioxydodecanoate

收率 79.0%

溶剂

benzene

反应条件

后处理

1. 1
   其他The solvent was removed
2. 2
   workup.ADDITIONthe residue was diluted with 50 mL ethyl acetate
3. 3
   洗涤The solution was washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
4. 4
   干燥the organic phase was dried over MgSO4
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by flash chromatography (hexane/EtOAc 8:1, Rf=0.21)

实验过程

The mixture of ethyl 3-oxododecanoate (1.456 g, ca. 5 mmol), ethylene glycol (2.78 mL, 50 mmol) and a catalytic amount of p-TsOH (95 mg, 0.5 mmol) in benzene (50 mL) was heated to 110° C. under an argon atmosphere overnight. The solvent was removed, and the residue was diluted with 50 mL ethyl acetate. The solution was washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL), and the organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography (hexane/EtOAc 8:1, Rf=0.21) to give ethyl 3,3-ethylenedioxydodecanoate (1.131 g, 3.95 mmol) in 79% overall yield for the above two steps. 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7 Hz, 3H), 1.20-1.44 (m, 17H), 1.76-1.82 (m, 2H), 2.65 (s, 2H), 3.94-4.04 (m, 4H), 4.16 (q, J=7 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 14.1, 22.6, 23.4, 29.22, 29.43, 29.48, 29.62, 31.8, 37.7, 42.5, 60.4, 65.0, 109.4, 169.5.

来源