Reacción #155421

Ecuación de reacción

N2

4-hydroxybenzaldehyde

pyridine

ethyl chloroformate

→

ethyl 4-formylphenyl carbonate

Rendimiento 92.0%

Disolventes

CH2Cl2

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 250 mL dry round bottom flask
2. 2
   TemperaturaThe solution was cooled in an ice-water bath
3. 3
   workup.STIRRINGThe mixture was stirred
4. 4
   workup.STIRRINGstirred at room temperature overnight
5. 5
   Otrothe CH2Cl2 layer was separated
6. 6
   ExtracciónThe aqueous layer was extracted continually with CH2Cl2 (100 mL×2)
7. 7
   SecadoThe combined CH2Cl2 solution was dried over Na2SO4
8. 8
   OtroAfter removal of the solvent
9. 9
   Otrothe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

Procedimiento

To a 250 mL dry round bottom flask were added 4-hydroxybenzaldehyde (6.11 g, 50.0 mmol), anhydrous CH2Cl2 (150 mL). The solution was cooled in an ice-water bath, then pyridine (4.86 mL, 60.0 mmol) was added. To the resulting solution, ethyl chloroformate (4.78 mL, 50.0 mmol) was added slowly under stirring and N2. The mixture was stirred and warmed to room temperature, then stirred at room temperature overnight. To the reaction mixture, water (100 mL) was added and the CH2Cl2 layer was separated. The aqueous layer was extracted continually with CH2Cl2 (100 mL×2). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give ethyl 4-formylphenyl carbonate (8.92 g) as colorless oil. Yield: 92%. 1H NMR (CDCl3, 300 MHz): δ=10.07 (s, 1H), 8.00 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.7 Hz, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.47 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3, 75.5 MHz): δ=191.0, 155.7, 152.9, 134.2, 131.4, 121.9, 65.4, 14.3.

Fuente