Methyl 4-chloro-3-nitrobenzoate → Methyl 4-methoxy-3-nitrobenzoate

HRID 1456839Notes

Reaction equation

HRID 1456839 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1Cl)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].[CH3:15][O-:16].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:16][CH3:15])[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 735797Methyl 4-chloro-3-nitrobenzoate2×HCID 10942334Sodium Methoxide

Product 1

HCID 602104Methyl 4-methoxy-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-nitro-4-chlorobenzoate (COMPOUND XIII) (see above for synthesis of 4-chloro-anti-CG) (1 equivalent) is treated with sodium methoxide (1.1 equivalent) in methanol with heating to produce the methyl 3-nitro-4-methoxybenzoate (COMPOUND XIV) which is purified by column chromatography and/or crystallization.

Workup

  1. temperaturewith heating

Sources & evidence

ORD record
ord-338e1f8ba593439d9dc45880a5dff4b4
Source dataset
uspto-grants-1998_12
Patent number
US05844110

Reaction notes

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