반응 #155421

반응 방정식

N2

4-hydroxybenzaldehyde

pyridine

ethyl chloroformate

→

ethyl 4-formylphenyl carbonate

수율 92.0%

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 stirred
4. 4
   workup.STIRRINGstirred at room temperature overnight
5. 5
   기타the CH2Cl2 layer was separated
6. 6
   추출The aqueous layer was extracted continually with CH2Cl2 (100 mL×2)
7. 7
   건조The combined CH2Cl2 solution was dried over Na2SO4
8. 8
   기타After removal of the solvent
9. 9
   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), anhydrous CH2Cl2 (150 mL). The solution was cooled in an ice-water bath, then pyridine (4.86 mL, 60.0 mmol) was added. To the resulting solution, ethyl chloroformate (4.78 mL, 50.0 mmol) was added slowly under stirring and N2. The mixture was stirred and warmed to room temperature, then stirred at room temperature overnight. 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 ethyl 4-formylphenyl carbonate (8.92 g) as colorless oil. Yield: 92%. 1H NMR (CDCl3, 300 MHz): δ=10.07 (s, 1H), 8.00 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.7 Hz, 2H), 4.42 (q, J=7.2 Hz, 2H), 1.47 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3, 75.5 MHz): δ=191.0, 155.7, 152.9, 134.2, 131.4, 121.9, 65.4, 14.3.

출처