Water → 2-Nitrobenzoic acid

HRID 2414203Notes

Reaction equation

HRID 2414203 reaction equation
CC[O:3][CH2:4][CH3:5].[OH-:6].[K+].[N+:8]([C:11]1C=[CH:15][CH:14]=[CH:13][C:12]=1C)([O-:10])=[O:9].O>CO>[N+:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=1[C:4]([OH:3])=[O:6])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 69442-NitrotolueneHCID 14797Potassium Hydroxide2×

Product 1

HCID 110872-Nitrobenzoic acidYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A catalytic amount of a metal catalyst (0.01 g metal porfin or 0.005 g metal (AcAc)2 +0.01 g crown-ether) was added to a 33% methanolic KOH-solution, (34 g KOH in 100 ml methanol). The reaction mixture was cooled to 25° C., 2-nitrotoluene (13.7 g, 0.1 mol) was added and air was passed through the reaction mixture, the temperature of the reaction mixture being kept at 25° C. After 12 hours the passsing through of air was interrupted and 150 ml water and 50 ml methanol was added. The reaction mixture was filtered. The filter layer was dissolved in boiling toluene (benzene), was filtered when hot, was cooled and was filtered again. Recrystallisation from ethanol gave a product with m.p. 120°-121° C. Yield 24-27%. As a by-product o-nitrobenzoic acid was formed.

Workup

  1. custombeing kept at 25° C
  2. filtrationThe reaction mixture was filtered
  3. dissolutionThe filter layer was dissolved
  4. filtrationwas filtered when hot
  5. temperaturewas cooled
  6. filtrationwas filtered again
  7. customRecrystallisation from ethanol
  8. customgave a product with m.p. 120°-121° C

Sources & evidence

ORD record
ord-8d8e4eb0139d487bb20ba84c56e54e75
Source dataset
uspto-grants-1988_01
Patent number
US04721821

Reaction notes

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