Reacción #1869152

Ecuación de reacción

ethyl 3-oxododecanoate

ethylene glycol

p-TsOH

→

ethyl 3,3-ethylenedioxydodecanoate

Rendimiento 79.0%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente