Nitric Acid → 4-Chloro-3-nitrobenzoic acid

HRID 1763056Notes

Reaction equation

HRID 1763056 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 63184-Chlorobenzoic Acid

Product 1

HCID 73204-Chloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
37 °C

Procedure

To a 2-liter, 3-necked, round-bottom flask is added 680 ml of concentrated H2SO4 and 400 g of p-chlorobenzoic acid. The mixture is stirred and brought to 0° C. by means of a constant temperature bath. A solution of concentrated HNO3 (216 ml) and concentrated H2SO4 (216 ml) is added dropwise to the reaction mixture at such a rate as to maintain the temperature between 10° C. and 25° C. Upon completion of the addition, the reaction temperature is raised to 37° C. and the mixture is allowed to stir for a period of 10-14 hours. The reaction mixture is then poured over crushed ice and the product, 4-chloro-3-nitrobenzoic acid, is filtered and dried, having a yield of 525.7 g or 98.7 percent with a melting point of 178° C.-180° C. This material is used without further purification.

Workup

  1. custombrought to 0° C. by means of a constant temperature bath
  2. temperatureto maintain the temperature between 10° C. and 25° C
  3. additionUpon completion of the addition
  4. stirringto stir for a period of 10-14 hours
  5. additionThe reaction mixture is then poured
  6. customover crushed ice
  7. filtrationthe product, 4-chloro-3-nitrobenzoic acid, is filtered
  8. customdried
  9. customThis material is used without further purification

Sources & evidence

ORD record
ord-635ae4beec0a4f5d9ddaa717a0fdcc78
Source dataset
uspto-grants-1989_05
Patent number
US04835306

Reaction notes

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