Реакция #155418

Уравнение реакции

4-hydroxybenzaldehyde

CH2Cl2

pyridine

isopropyl chloroformate

→

4-formylphenyl isopropyl carbonate

Выход 100.0%

Растворители

toluene

MTBE

water

Условия реакции

Обработка

1. 1
   ДругоеTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 2 hours
3. 3
   ДругоеThe aqueous layer was separated
4. 4
   Промывкаthe MTBE layer was washed
5. 5
   СушкаThe organic layer was dried over Na2SO4
6. 6
   Другоеthe solvent was evaporated

Методика

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).

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