Hydrochloric Acid → 2,4-Dimethoxy-5-nitrobenzoic acid

Reaction equation

[Na].Cl[C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:15][CH3:16])[CH:4]=1.Cl.[CH3:18][OH:19]>>[CH3:16][O:15][C:5]1[CH:4]=[C:3]([O:19][CH3:18])[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 5360545Sodium

HCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acid

Product 1

HCID 133076602,4-Dimethoxy-5-nitrobenzoic acid

Procedure

In a stream of argon, 0.30 g of metallic sodium was added to 5 ml of methanol under ice-cooling, the mixture was stirred at room temperature for a while and then 1.00 g of 4-chloro-2-methoxy-5-nitrobenzoic acid was added to the resulting solution in small portions, followed by stirring at 80° C. for 8 hours. After completion of the reaction, the reaction solution was poured into 1N hydrochloric acid aqueous solution, and the thus precipitated product of interest was collected by filtration, washed with water and then dried under a reduced pressure to give 0.80 g of 2,4-dimethoxy-5-nitrobenzoic acid.