5-Ethoxycarbonyloxy-2-nitrobenzoic acid → 5-Hydroxy-2-nitrobenzoic acid

HRID 851349Notes

Reaction equation

HRID 851349 reaction equation
C(OC([O:6][C:7]1[CH:8]=[CH:9][C:10]([N+:16]([O-:18])=[O:17])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13])=O)C>[OH-].[K+].O>[C:12]([C:11]1[CH:15]=[C:7]([OH:6])[CH:8]=[CH:9][C:10]=1[N+:16]([O-:18])=[O:17])([OH:14])=[O:13]

Participants

4

Reactant 1

HCID 205022675-Ethoxycarbonyloxy-2-nitrobenzoic acid

Product 1

HCID 118825-Hydroxy-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

5-Ethoxycarbonyloxy-2-nitrobenzoic acid (6.12 g) was dissolved in a solution of potassium hydroxide (3.2 g of 85% pure material) in water (10 ml) and heated under reflux for 2 hours, to cleave off the ethoxy-carbonyl residue and form the di-potassium salt of 3-carboxy-4-nitrophenol. The solution so prepared was mixed with toluene and distilled until the water had been removed. Dimethyl sulphoxide (50 ml) was added and the mixture distilled until the vapour temperature reached 190°. A further quantity (50 ml) of dimethyl sulphoxide (50 ml) was then added, together with 3-chloro-4,5-difluorobenzotrifluoride (5.43 g), and the mixture heated at 100° for 4 hours. The mixture was diluted with water (200 ml) and acidified with dilute hydrochloric acid. The mixture was extracted twice with ether and the extracts washed with water, dried and evaporated. The brown oil remaining was crystallised from carbon tetrachloride to give the required compound (2 g) with a melting point of 145°-148°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-b3e59380378147899641a9844a0ff1da
Source dataset
uspto-grants-1983_05
Patent number
US04384135

Reaction notes

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