Hydrochloric Acid → 3-Hydroxy-4-methyl-2-nitrobenzoic acid

HRID 1672477

Reaction equation

HRID 1672477 reaction equation
C(N[C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])(=O)C.[OH-:18].[K+].Cl>O>[OH:18][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2434333-Acetamido-4-methyl-2-nitrobenzoic acid

Product 1

HCID 813743-Hydroxy-4-methyl-2-nitrobenzoic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-(acetylamino)-4-methyl-2-nitrobenzoic acid (237.5 g, 0.997 mol) and KOH (451.2 g, 8.04 mol) in water (2830 mL) was refluxed for 48 h. The dark red solution was cooled and acidified to pH 1 with concentrated HCl. The yellow solid was filtered and re-crystallized from water (1800 mL) to give the title compound (183 g, 93.4%) as a yellow solid.

Workup

  1. temperatureThe dark red solution was cooled
  2. filtrationThe yellow solid was filtered
  3. customre-crystallized from water (1800 mL)

Sources & evidence

ORD record
ord-38c31f1419744cd699942a50b6d9a0af
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Linked notes

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