Réaction #155417

Équation de réaction

N2

4-hydroxybenzaldehyde

pyridine

octanoyl chloride

→

4-formylphenyl octanoate

Rendement 86.2%

Solvants

CH2Cl2

water

Conditions de réaction

Traitement

1. 1
   AutreTo a 250 mL dry round bottom flask
2. 2
   TempératureThe solution was cooled in an ice-water bath
3. 3
   workup.STIRRINGThe mixture was first stirred at 0° C. for 2 hours
4. 4
   Autrethe CH2Cl2 layer was separated
5. 5
   ExtractionThe aqueous layer was extracted continually with CH2Cl2 (100 mL×2)
6. 6
   SéchageThe combined CH2Cl2 solution was dried over Na2SO4
7. 7
   AutreAfter removal of the solvent
8. 8
   Autrethe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

Mode opératoire

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.

Source