Sulfuric Acid → Methyl 2-chloro-3-nitrobenzoate

HRID 2257693Notes

Reaction equation

HRID 2257693 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[C:19](OC)(OC)(OC)C>CO>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15050Trimethyl orthoacetateHCID 198702-Chloro-3-nitrobenzoic acid

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

25.50 g (0,127 mol) of 2-chloro-3-nitrobenzoic acid are dissolved in 50 ml of MeOH, and 3 ml of concentrated sulfuric acid are added. The reaction mixture is heated at boiling for 4 h. Following the addition of 10 ml of trimethyl orthoacetate the mixture is heated at boiling for a further 2 h. After cooling to 0° C. and filtering off the solid by suction, 26.4 g (96 %) of colorless methyl 2-chloro-3-nitrobenzoate are obtained, m.p. 68-70° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureis heated
  3. waitat boiling for a further 2 h
  4. filtrationfiltering off the solid by suction, 26.4 g (96 %) of colorless methyl 2-chloro-3-nitrobenzoate
  5. customare obtained

Sources & evidence

ORD record
ord-0d0a3652061f45d3b53b248a1b5d377c
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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