Réaction #67410

Équation de réaction

1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester

HNO3

HCl

→

1-(4-methoxy-3-nitro-phenyl)-cyclopropanecarboxylic acid methyl ester

Rendement 98.1%

Solvants

Ac2O

AcOH

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise at 0° C
2. 2
   ExtractionThe resulting mixture was extracted with EtOAc (200 mL×3)
3. 3
   LavageThe organic layer was washed with sat. aq. NaHCO3
4. 4
   Séchagebrine, dried over anhydrous Na2SO4
5. 5
   Autreevaporated under vacuum

Mode opératoire

To a solution of 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (30.0 g, 146 mmol) in Ac2O (300 mL) was added a solution of HNO3 (14.1 g, 146 mmol, 65%) in AcOH (75 mL) at 0° C. The reaction mixture was stirred at 0˜5° C. for 3 h before aq. HCl (20%) was added dropwise at 0° C. The resulting mixture was extracted with EtOAc (200 mL×3). The organic layer was washed with sat. aq. NaHCO3 then brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(4-methoxy-3-nitro-phenyl)-cyclopropanecarboxylic acid methyl ester (36.0 g, 98%), which was directly used in the next step. 1H NMR (CDCl3, 300 MHz) δ 7.84 (d, J=2.1 Hz, 1H), 7.54 (dd, J=2.1, 8.7 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 3.97 (s, 3H), 3.65 (s, 3H), 1.68-1.64 (m, 2H), 1.22-1.18 (m, 2H).

Source