Nitric Acid → Ethyl 4,5-diethoxy-2-nitrobenzoate

HRID 871261Notes

Reaction equation

HRID 871261 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[N+:18]([O-])([OH:20])=[O:19]>CC(O)=O>[CH2:16]([O:15][C:14]1[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1)[CH3:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 586407Ethyl 3,4-diethoxybenzoate

Product 1

HCID 11022393Ethyl 4,5-diethoxy-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-diethoxybenzoate (6.43 g, 27 mmol) in AcOH (50 mL) was dropped fuming nitric acid (90%, 6.3 g) and the reaction was heated at 50° C. overnight, to afford ethyl 4,5-diethoxy-2-nitrobenzoate as a solid (7.175 g, 94%). 1H NMR (300 MHz, CDCl3) δ 7.44 (s, 1H), 7.05 (s, 1H), 4.37 (q, 2H), 4.18 (m, 4H), 1.50 (m, 6H), 1.35 (t, 3H); LC-MS (ESI) m/z 284 (M+H)+.

Sources & evidence

ORD record
ord-5303ae23e3ae4a2fa2f831ba08c1e2ba
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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