Ethanol → Ethyl 2-chloro-4-hydroxybenzoate

HRID 1442478Notes

Reaction equation

HRID 1442478 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>O>[CH2:17]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[Cl:1])[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 19981058Ethyl 2-chloro-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of 34.5 g (200 mmol) of 2-chloro-4-hydroxy-benzoic acid, 5 mL of concentrated sulfuric acid and 400 mL of ethanol was refluxed for 18 hours. 1.2 L of water were added to the resulting mixture followed by extraction with 1.5 L of methylene chloride. The mixture was then washed with aqueous sodium bicarbonate solution and water and dried with magnesium sulfate followed by distilling off the solvent. The residue was recrystallized from hexane/ethyl acetate to obtain 20.4 g of a light orange solid.

Workup

  1. temperaturewas refluxed for 18 hours
  2. extractionfollowed by extraction with 1.5 L of methylene chloride
  3. washThe mixture was then washed with aqueous sodium bicarbonate solution and water
  4. dry with materialdried with magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-22eabb4dce4d4a8ea018e7cf9cb24236
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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