Nitric Acid → Methyl 5-chloro-2-hydroxy-3-nitrobenzoate

HRID 329716Notes

Reaction equation

HRID 329716 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 235651Methyl 5-chloro-2-hydroxy-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 100 g of methyl 5-chlorosalicylate and 250 ml of concentrated sulfuric acid (while keeping at a temperature below 0° C.) is added dropwise a mixture of 25 ml of funing nitric acid (d 1.50) and 25 ml of concentrated sulfuric acid at a temperature below 5° C. The resultant solution is stirred under ice cooling for 0.5 hour and poured into ice-cold water. The precipitated crystals are collected by filtration and dried to give 122 g of methyl 5-chloro-3-nitrosalicylate, melting at 108°-110° C.

Workup

  1. customwhile keeping at a temperature below 0° C.
  2. additionis added dropwise
  3. additionpoured into ice-cold water
  4. filtrationThe precipitated crystals are collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-ae3aac29731c497b9ef7552f2d76ed5e
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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