Reacción #155418

Ecuación de reacción

4-hydroxybenzaldehyde

CH2Cl2

pyridine

isopropyl chloroformate

→

4-formylphenyl isopropyl carbonate

Rendimiento 100.0%

Disolventes

toluene

MTBE

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 2 hours
3. 3
   OtroThe aqueous layer was separated
4. 4
   Lavadothe MTBE layer was washed
5. 5
   SecadoThe organic layer was dried over Na2SO4
6. 6
   Otrothe solvent was evaporated

Procedimiento

To a 250 mL dry round bottom flask were added 4-hydroxybenzaldehyde (4.88 g, 40.0 mmol), anhydrous CH2Cl2 (40 mL) and pyridine (4.2 mL, 52.0 mmol). The mixture was stirred in an ice-water bath, then a solution of isopropyl chloroformate in toluene (1.0 M, 48.0 mL) was added. After stirring at 0° C. for 2 hours, water (100 mL) and MTBE (300 mL) were added to the reaction mixture. The aqueous layer was separated, and the MTBE layer was washed, respectively, with cold water (80 mL), cold 5% NaOH aqueous solution (80 mL), cold water (80 mL), cold 0.5 N HCl aqueous solution (80 mL) and cold water (80 mL). The organic layer was dried over Na2SO4, and the solvent was evaporated to give 4-formylphenyl isopropyl carbonate (8.50 g) as pale yellow oil. Yield: 100%. 1H NMR (CDCl3, 300 MHz): δ=9.71 (s, 1H), 7.64 (d, J=8.4 Hz, 2H), 7.10 (d, J=8.7 Hz, 2H), 4.73 (seventet, J=6.0 Hz, 1H), 1.12 (d, J=6.3 Hz, 6H).

Fuente