Ethanol → Ethyl 4-chloro-3-nitrobenzoate

HRID 1181311Notes

Reaction equation

HRID 1181311 reaction equation
[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].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH3:20])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 73204-Chloro-3-nitrobenzoic acid

Product 1

HCID 1268247Ethyl 4-chloro-3-nitrobenzoateYield 97%

Procedure

4-Chloro-3-nitrobenzoic acid (300 g) was dissolved in ethyl alcohol (1500 ml) and concentrated sulfuric acid (100 ml) was added with ice-cooling. The mixture was refluxed under heating for 7 hr. The reaction mixture was poured into ice-cold water and the precipitated crystals were collected by filtration to give the title compound (332 g, yield 97%).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 7 hr
  4. additionThe reaction mixture was poured into ice-cold water
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ddb78582164f41519617d6ca4b602f16
Source dataset
uspto-grants-2007_10
Patent number
US07285551B2

Reaction notes

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