Reacción #64664

Ecuación de reacción

ethyl 3,3-diethoxypropionate

benzyl alcohol

→

ethyl 3,3-dibenzyloxypropionate

Rendimiento 99.6%

Ethyl 3,3-dibenzyloxypropionate

Rendimiento 99.6%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONthe solvent was distilled from the reaction mixture in 1.5 h period
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in ether (@ 300 mL)
3. 3
   Lavadowashed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
4. 4
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Otrothe solvent removed in vacuo

Procedimiento

To a 1000 mL round-bottomed flask was added ethyl 3,3-diethoxypropionate (20.0 g, 0.1051 mole), benzyl alcohol (22.7 g, 0.2102 mole), p-toluenesulfonic acid monohydrate (0.5 g, 0.0026 mole) and benzene (350 mL). Heating the mixture at 80° C., the solvent was distilled from the reaction mixture in 1.5 h period. The resulting residue was dissolved in ether (@ 300 mL) and washed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and the solvent removed in vacuo to give ethyl 3,3-dibenzyloxypropionate (9) as a colorless oil (32.9 g, 99.5% yield): 1H NMR (CDCl3) d 1.22 (t, 3H, J=7.2 Hz), 2.79 (d, 2H, J=5.9 Hz), 4.12 (q, 2H, J=7.2 Hz), 4.60 (d, 2H, J=11.6 Hz), 4.70 (d, 2H, J=11.6 Hz), 5.22 (t, 1H, J=6 Hz), 7.27-7.36 (m, 10H); IR (Neat) 3100, 3080, 3040, 2990, 2940, 2920, 2885, 1740, 1630, 1458, 1375, 1315, 1190, 1120, 1050, 1030, 740, 700. ##STR8##

Fuente