Benzoic Acid → 3-Nitrobenzoic acid

HRID 259088Notes

Reaction equation

HRID 259088 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>ClCCCl>[N+:10]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([OH:9])=[O:8])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 944Nitric AcidHCID 1118Sulfuric Acid

Product 1

HCID 84973-Nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

61 g of benzoic acid were suspended in 200 ml of 1,2-dichloroethane. The suspension was heated to 40° C. following the addition of 38.6 g (0.60 mol) of 98% nitric acid. 63.5 g of 100% sulphuric acid were then added dropwise over a period of 2 hours at that temperature, followed by stirring for another 3 hours. After cooling to 20° C., the deposit was filtered off. The filter residue was washed four times with 4 × 25 ml of 1,2-dichloroethane and then with water, followed by drying at 90° C. 32.6 g (39% of the theoretical yield) of 3-nitrobenzoic acid were obtained in this way.

Workup

  1. temperatureAfter cooling to 20° C.
  2. filtrationthe deposit was filtered off
  3. washThe filter residue was washed four times with 4 × 25 ml of 1,2-dichloroethane
  4. customby drying at 90° C

Sources & evidence

ORD record
ord-0951bfd1f5314031b4656a429ff0c7c2
Source dataset
uspto-grants-1977_07
Patent number
US04036838

Reaction notes

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