Reaction #89918

Reaction equation

NaOH

NaOH

HNO3

NaHCO3

benzyl 3-(benzyloxy)-4-methoxybenzoate

→

benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate

Yield 93.0%

Solvents

Ac2O

Conditions

Workup

1. 1
   workup.WAITat RT for 3 hours
2. 2
   ExtractionThe mixture was extracted with CH2Cl2 (3×200 mL)
3. 3
   DryingThe combined organics were dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe residue was azeotroped with heptane

Procedure

To a solution of benzyl 3-(benzyloxy)-4-methoxybenzoate (6.32 g, 18.1 mmol) in Ac2O (62 mL) cooled to −10° C. under an atmosphere of N2 was added fuming HNO3 (1.5 mL, 37.1 mmol) in one portion. Stirring was continued at −10° C. for 10 minutes, then at RT for 3 hours. The reaction mixture was carefully poured into ice-water and the pH adjusted to ca. pH=5 with 5N NaOH, sat. NaHCO3 and 0.5 NaOH. The mixture was extracted with CH2Cl2 (3×200 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The residue was azeotroped with heptane to give benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate as red colored oil (6.55 g, 16.7 mmol, 93%).

Source