Nitric Acid → Ethyl 4-chloropropoxy-3-methoxy-2-nitrobenzoate

HRID 384751Notes

Reaction equation

HRID 384751 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][C:7]=1[O:17][CH3:18].[N+:19]([O-])([OH:21])=[O:20]>ClCCl.C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([N+:19]([O-:21])=[O:20])[C:7]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 10923703Ethyl 4-(3-chloropropoxy)-3-methoxybenzoate

Product 1

HCID 69767630Ethyl 4-chloropropoxy-3-methoxy-2-nitrobenzoateYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

WO 02/36587 describes a process for preparing a 5-alkoxy-4-halogenoalkoxy-2-nitrobenzoic acid compound from a 3-alkoxy-4-hydroxybenzoic acid compound. For example, ethyl vanillate (i.e., ethyl 4-hydroxy-3-methoxybenzoate) is reacted with 3-bromo-1-chloropropane in an aqueous potassium carbonate solution in the presence of N-butyl-ammonium bromide to produce ethyl 4-(3-chloropropoxy)-3-methoxybenzoate, and the ethyl 4-(3-chloropropoxy)-3-methoxybenzoate is reacted with 70% nitric acid in a mixture of dichloromethane and acetic acid, to give ethyl 4-chloropropoxy-3-methoxy-2-nitrobenzoate in 82% yield (based on the amount of ethyl vanillate).

Sources & evidence

ORD record
ord-49bf6d11dccc460aad546ebb0f94edf4
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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