Hydrochloric Acid → 5-Hydroxy-2-nitrobenzoic acid

HRID 1439605Notes

Reaction equation

HRID 1439605 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[OH-:14].[K+].O.Cl>CS(C)=O>[OH:14][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 118825-Hydroxy-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-2-nitrobenzoic acid (100 g) in 800 ml dimethylsulfoxide was treated with 112 g powdered KOH with cooling, 170 ml anhydrous alcohol added and the mixture stirred 2 hours at 25° and then left overnight. The mixture was kept at 28° for about 8 hours, then overnight at 0°, warmed to room temperature and 3.5 liters of water added. The mixture was acidified with HCl, 1 kg NcCl added and extracted with ethyl acetate. The extract was washed with water, dried, 50 g KHCO3 in 500 ml water added, diluted to 2 liters, and the ethyl acetate blown off with a stream of nitrogen. The solution was acidified and filtered to give 56 g product, m.128-30°.

Workup

  1. temperaturewith cooling
  2. waitleft overnight
  3. waitThe mixture was kept at 28° for about 8 hours
  4. additionadded
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. addition50 g KHCO3 in 500 ml water added
  9. additiondiluted to 2 liters
  10. filtrationfiltered

Sources & evidence

ORD record
ord-c569a7de8e1d409894b3f07d1251c335
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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