Ethanol → Ethyl 5-chlorosalicylate

HRID 1870271Notes

Reaction equation

HRID 1870271 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH2:17][CH3:18])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 94475-Chlorosalicylic Acid

Product 1

HCID 306053Ethyl 5-chlorosalicylateYield 88%

Procedure

To a suspension of 5-chlorosalicylic acid (500 g) in ethanol (2 L) was added concentrated sulphuric acid (40 ml) with stirring at room temperature. After the reaction mixture was refluxed for 12 hours, the solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with 10% NaCl solution and 4% sodium hydrogen carbonate solution, and then evaporated under reduced pressure, dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure to give the title compound (514 g, 88%) as a pale-yellow oil.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 12 hours
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with 10% NaCl solution and 4% sodium hydrogen carbonate solution
  5. customevaporated under reduced pressure
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fae1e5bfdf5f4b86be9d5e90ac472234
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

Loading…