반응 #1869152

반응 방정식

ethyl 3-oxododecanoate

ethylene glycol

p-TsOH

→

ethyl 3,3-ethylenedioxydodecanoate

수율 79.0%

용매

benzene

반응 조건

후처리

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

실험 절차

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.

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