Methanol → Methyl 2-chloro-5-nitrobenzoate

HRID 2396163Notes

Reaction equation

HRID 2396163 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 22754Methyl 2-chloro-5-nitrobenzoateYield 68%

Procedure

A mixture of 2-chloro-5-nitrobenzoic acid (70.0 g, 0.35 mol), 280 ml of methanol and 27 ml of concentrated sulfuric acid is added to a 500 ml, three-necked round-bottom flask equipped with an overhead stirrer and condenser, and the solution is stirred and heated at reflux for 24 hours. After the solution cools, yellow crystals form and are collected by filtration. The product is washed with water and recrystallized from ethyl acetate/hexane to yield 68 percent of yellow crystals: mp 69.5°-70.0°.

Workup

  1. additionis added to a 500 ml, three-necked round-bottom flask
  2. customequipped with an overhead stirrer and condenser
  3. temperatureheated
  4. temperatureat reflux for 24 hours
  5. filtrationAfter the solution cools, yellow crystals form and are collected by filtration
  6. washThe product is washed with water
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b4affa6b855a4e62bee794ee4675d79d
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

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