Реакция #155417

Уравнение реакции

N2

4-hydroxybenzaldehyde

pyridine

octanoyl chloride

→

4-formylphenyl octanoate

Выход 86.2%

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 (100 mL×2)
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 4-hydroxybenzaldehyde (6.11 g, 50.0 mmol) and anhydrous CH2Cl2 (50 mL). The solution was cooled in an ice-water bath, then pyridine (8.09 mL, 100 mmol) was added. To the resulting solution, octanoyl chloride (10.3 mL, 60 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 (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 4-formylphenyl octanoate (10.7 g) as colorless oil. Yield: 86%. 1H NMR (CDCl3, 300 MHz): δ=9.98 (s, 1H), 7.91 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 2.58 (t, J=6.9 Hz, 2H), 1.38-0.86 (m, 13H). 13C NMR (CDCl3, 75.5 MHz): δ=191.0, 171.7, 155.6, 134.0, 131.3, 122.5, 34.5, 31.7, 29.1, 29.0, 24.9, 22.7, 14.2.

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