Ethanol → Ethyl 2-chloro-5-hydroxybenzoate

HRID 1526429Notes

Reaction equation

HRID 1526429 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17][CH2:18]O>>[CH2:17]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4582102-Chloro-5-hydroxybenzoic acid

Product 1

HCID 24820325Ethyl 2-chloro-5-hydroxybenzoate

Procedure

To a mixture of commercially available 2-chloro-5-hydroxybenzoic acid (4 g, 23.18 mmol) in dry EtOH (90 mL), concentrated sulphuric acid (1 mL, 17.62 mmol) was added. The mixture was stirred under reflux overnight, then solvent evaporated under reduced pressure and the residue dissolved with DCM. A saturated solution of NaHCO3 was added, phases were separated, organics dried over sodium sulphate, filtered and evaporated to obtain 5 g of the corresponding 2-chloro-5-hydroxy-benzoic acid ethyl ester.

Workup

  1. additionwas added
  2. temperatureunder reflux overnight
  3. customsolvent evaporated under reduced pressure
  4. dissolutionthe residue dissolved with DCM
  5. additionA saturated solution of NaHCO3 was added
  6. customphases were separated
  7. dry with materialorganics dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-7e809c3434814ea1ad68fb0cd0f62c90
Source dataset
uspto-grants-2015_07
Patent number
US09085584B2

Reaction notes

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