Ethanol → Ethyl 4-chloro-3-nitrobenzoate

HRID 1788403Notes

Reaction equation

HRID 1788403 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]>>[CH2:19]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:20]

Participants

4

Reactant 3

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

Product 1

HCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Procedure

4-chloro-3-nitrobenzoic acid (100 g) was dissolved in 500 mL anhydrous ethanol and 35 mL concentrated sulfuric acid was added dropwise over a period of 5 minutes. The mixture was refluxed overnight then poured on 1 L ice. The precipitate was separated by filtration, washed four times with water and was then air dried. Recrystallization from 275 mL ethanol afforded a pale yellow product.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe precipitate was separated by filtration
  3. washwashed four times with water
  4. customair dried
  5. customRecrystallization from 275 mL ethanol
  6. customafforded a pale yellow product

Sources & evidence

ORD record
ord-f2ede4b4f4be459a9770a97f6390fb5a
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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