반응 #155417

반응 방정식

N2

4-hydroxybenzaldehyde

pyridine

octanoyl chloride

→

4-formylphenyl octanoate

수율 86.2%

용매

CH2Cl2

water

반응 조건

후처리

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

실험 절차

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.

출처