Реакция #155420

Уравнение реакции

N2

3-hydroxybenzaldehyde

pyridine

butyryl chloride

→

3-formylphenyl butyrate

Выход 75.0%

Растворители

CH2Cl2

water

Условия реакции

Обработка

1. 1
   ДругоеTo a 250 mL dry round bottom flask
2. 2
   ТемператураThe solution was cooled in an ice-water bath
3. 3
   workup.STIRRINGThe mixture was first stirred at 0° C. for 2 hours
4. 4
   Другоеthe CH2Cl2 layer was separated
5. 5
   ЭкстракцияThe aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
6. 6
   СушкаThe combined CH2Cl2 solution was dried over Na2SO4
7. 7
   ДругоеAfter removal of the solvent
8. 8
   Другоеthe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

Методика

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.

Источник