Ethanol → Benzoic acid, 2-chloro-5-methyl-, ethyl ester

HRID 42000Notes

Reaction equation

HRID 42000 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH2:17](O)[CH3:18]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2404302-Chloro-5-methylbenzoic Acid

Product 1

HCID 20729316Benzoic acid, 2-chloro-5-methyl-, ethyl esterYield 96%

Procedure

To a solution of 2-chloro-5-methylbenzoic acid (7.62 mmol, 1.30 g) in ethanol (16 ml), H2SO4 (35 mmol, 1.82 ml) was added and the mixture was refluxed for 20 hours. The solvent was evaporated and the crude residue was dissolved in water. The solution neutralised with 6N NaOH aqueous solution and extracted with CHCl3. The organic phase was evaporated affording 1.46 g (yield 96%) of the expected product.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude residue was dissolved in water
  4. extractionextracted with CHCl3
  5. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-4c01781109a24193b9802ea64ff61c37
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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