Reacción #155420

Ecuación de reacción

N2

3-hydroxybenzaldehyde

pyridine

butyryl chloride

→

3-formylphenyl butyrate

Rendimiento 75.0%

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 first stirred at 0° C. for 2 hours
4. 4
   Otrothe CH2Cl2 layer was separated
5. 5
   ExtracciónThe aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
6. 6
   SecadoThe combined CH2Cl2 solution was dried over Na2SO4
7. 7
   OtroAfter removal of the solvent
8. 8
   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 3-hydroxybenzaldehyde (5.0 g, 41.0 mmol), anhydrous CH2Cl2 (50 mL). The solution was cooled in an ice-water bath, then pyridine (6.64 mL, 82.0 mmol) was added. To the resulting solution, butyryl chloride (5.15 mL, 49.2 mmol) was added slowly under stirring and N2. The mixture was first stirred at 0° C. for 2 hours, then at room temperature for 20 hours. To the reaction mixture, water (80 mL) was added and the CH2Cl2 layer was separated. The aqueous layer was extracted continually with CH2Cl2 (50 mL×3). 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 3-formylphenyl butyrate (5.9 g) as colorless oil. Yield: 75%. 1H NMR (CDCl3, 300 MHz): δ=9.96 (s, 1H), 7.72 (t of d, J=1.2, 7.5 Hz, 1H), 7.60 (t, J=2.4 Hz, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.36-7.32 (m, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.78 (sextet, J=7.2 Hz, 2H), 1.04 (t, J=7.5 Hz, 3H). 13C NMR (CDCl3, 75.5 MHz): δ=191.2, 171.7, 151.3, 137.7, 130.1, 127.8, 127.2, 122.2, 36.0, 18.3, 13.5.

Fuente