Nitric Acid → Methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate

HRID 871291Notes

Reaction equation

HRID 871291 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10].[N+:18]([O-])([OH:20])=[O:19]>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([N+:18]([O-:20])=[O:19])=[C:8]([CH:7]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 11623039Methyl 3-(3-chloropropoxy)-4-methoxybenzoate

Product 1

HCID 11666631Methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoateYield 86%

Procedure

Methyl 3-(3-chloropropoxy)-4-methoxybenzoate (6.65 g, 25.7 mmol) was reacted with nitric acid as described in Example 16A Step 2 to give methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate (6.70 g, 22.1 mmol, 86%). 1H NMR (300 MHz, DMSO-d6) δ 7.65 (s, 1H), 7.37 (s, 1H), 4.26 (t, 2H), 3.89 (s, 3H), 3.81 (s, 3H), 3.76 (t, 2H), 2.26-2.18 (m, 2H).

Sources & evidence

ORD record
ord-a440f04267c746689e55899f0bfff641
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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