4-Hydroxy-3-nitrobenzoic acid → Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

HRID 354477Notes

Reaction equation

HRID 354477 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C1C=CC=CC=1.CO>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([O:8][CH3:15])=[O:7])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 120334-Hydroxy-3-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterYield 75.2%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a stirred solution of 4-hydroxy-3-nitrobenzoic acid (5.18 g, 28.29 mmol) in benzene-MeOH (4:1, v/v, 140 mL) was added TMSCHN2 (14.10 mL, 28.20 mmol, 2 M solution in hexane) at room temp, and the resulting mixture was stirred overnight. The mixture was evaporated and the residue was purified by column chromatography on silica-gel with CHCl3 as eluent to give 4.18 g (75%) methyl 3-nitro-4-hydroxybenzoate as a yellow crystalline solid. 1H-NMR (CDCl3) d 3.95 (s, 3H), 7.22 (d, 1H, J=8.8 Hz), 8.24 (dd, 1, J=2.0, 8.8 Hz), 8.83 (d, 1H, J=2.0 Hz), 10.89 (s, 1H).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica-gel with CHCl3 as eluent

Sources & evidence

ORD record
ord-c59c423fd790488d8f470cc71dbddfd2
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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