Nitric Acid → Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate

HRID 631230Notes

Reaction equation

HRID 631230 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][O:16][CH3:17].CC(OC(C)=O)=O.[N+:25]([O-])([OH:27])=[O:26]>CC(O)=O>[CH3:1][O:2][C:3]1[C:4]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:11]([N+:25]([O-:27])=[O:26])[CH:12]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 66876699Methyl 4-methoxy-3-(2-methoxyethoxy)benzoate

Product 1

HCID 58394383Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoateYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

According to the procedure described in Example 6A Step 2, to a solution of methyl 4-methoxy-3-(2-methoxyethoxyl)benzoate (5.6 g, 23.3 mmol) and Ac2O (12 mL) in AcOH (60 mL) was dropped fuming nitric acid (90%, 4 mL). The reaction was heated at 50° C. for 3 hours, and the residue was purified by silica gel chromatography with 0-15% EtOAc/hexane as eluants to afford methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate as a solid (3.67 g, 56%). 1H NMR (300 MHz, DMSO-d6) δ 7.64 (s, 1H), 7.34 (s, 1H), 4.26 (m, 2H), 3.91 (s, 3H), 3.82 (s, 3H), 3.68 (m, 2H), 3.33 (s, 3H).

Workup

  1. customthe residue was purified by silica gel chromatography with 0-15% EtOAc/hexane as eluants

Sources & evidence

ORD record
ord-36a5b0777f26438b816561aef9bfdfb2
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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