Nitric Acid → Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate

HRID 871254Notes

Reaction equation

HRID 871254 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N+:22]([O-])([OH:24])=[O:23]>CC(O)=O>[CH3:21][O:20][CH2:19][CH2:18][O:17][C:16]1[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2808992Ethyl 3,4-bis(2-methoxyethoxy)benzoate

Product 1

HCID 11186961Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoateYield 94%

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 ethyl 3,4-bis(2-methoxyethoxy)benzoate (7.87 g, 26.4 mmol) in AcOH (50 mL) was added HNO3 (90%, 4 mL) and the mixture was heated at 50° C. for 5 hours, to afford ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate as an oil (8.531 g, 94%). 1H NMR (300 MHz, CDCl3) δ 7.51 (s, 1H), 7.12 (s, 1H), 4.37 (q, 2H), 4.25 (m, 4H), 3.80 (m, 4H), 3.45 (s, 6H), 1.35 (t, 3H); LC-MS (ESI) m/z 344 (M+H)+.

Sources & evidence

ORD record
ord-6f03bda460f64bb0a619a5d1da011eca
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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