Reaction #155418

Reaction equation

4-hydroxybenzaldehyde

CH2Cl2

pyridine

isopropyl chloroformate

→

4-formylphenyl isopropyl carbonate

Yield 100.0%

Solvents

toluene

MTBE

water

Conditions

Workup

1. 1
   OtherTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 2 hours
3. 3
   OtherThe aqueous layer was separated
4. 4
   Washthe MTBE layer was washed
5. 5
   DryingThe organic layer was dried over Na2SO4
6. 6
   Otherthe solvent was evaporated

Procedure

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