Ethanol → ethyl 2-chloro-5-nitrobenzoate

HRID 2116549Notes

Reaction equation

HRID 2116549 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].C([O-])([O-])=O.[K+].[K+].[CH2:20](O)[CH3:21]>S(=O)(=O)(O)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][CH2:20][CH3:21])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 2774222ethyl 2-chloro-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-chloro-5-nitrobenzoic acid (26 g) in ethanol (260 mL) and concentrated sulfuric acid (1 mL) was heated at reflux for 18 hr. The reaction mixture was cooled and K2CO3 was added to quench the reaction. The resulting mixture was filtered and concentrated. The residue was then suspended in ether and filtered to remove insoluble starting acid. The filtrate was washed with 4% KOH (110 mL), dried over MgSO4 and concentrated to provide 16.2 g of ethyl 2-chloro-5-nitrobenzoate as a colorless oil which solidified on standing.

Workup

  1. temperatureat reflux for 18 hr
  2. temperatureThe reaction mixture was cooled
  3. customto quench
  4. customthe reaction
  5. filtrationThe resulting mixture was filtered
  6. concentrationconcentrated
  7. filtrationfiltered
  8. customto remove insoluble
  9. washThe filtrate was washed with 4% KOH (110 mL)
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-319b96eb17f84477a76ee7226ae0e324
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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