Réaction #155418

Équation de réaction

4-hydroxybenzaldehyde

CH2Cl2

pyridine

isopropyl chloroformate

→

4-formylphenyl isopropyl carbonate

Rendement 100.0%

Solvants

toluene

MTBE

water

Conditions de réaction

Traitement

1. 1
   AutreTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 2 hours
3. 3
   AutreThe aqueous layer was separated
4. 4
   Lavagethe MTBE layer was washed
5. 5
   SéchageThe organic layer was dried over Na2SO4
6. 6
   Autrethe solvent was evaporated

Mode opératoire

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).

Source