Sulfuric Acid → Methyl 2-chloro-4-nitrobenzoate

HRID 514841Notes

Reaction equation

HRID 514841 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[C:19](=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 74482-Chloro-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 83343Methyl 2-chloro-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-4-nitrobenzoic acid (10 g, 0.06 mol) in MeOH (120 mL) was added H2SO4 (5 mL). The resulting mixture was stirred at 60° C. overnight. After cooling to room temperature, the mixture was brought to pH=8 using sodium bicarbonate solution. After removal of MeOH, the resulting crude mixture was purified by column chromatography (20% CH2Cl2/PE) to afford 4 g of the title compound. LC-MS: m/z 216.6 (M+H)+

Workup

  1. temperatureAfter cooling to room temperature
  2. customAfter removal of MeOH
  3. customthe resulting crude mixture was purified by column chromatography (20% CH2Cl2/PE)

Sources & evidence

ORD record
ord-ecd0707642c6423386f50f630837b5f6
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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