Salicylic Acid → Ethyl Salicylate

HRID 1259021Notes

Reaction equation

HRID 1259021 reaction equation
OS(O)(=O)=O.[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9].[CH3:16][CH2:17]O>C(Cl)Cl>[OH:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 8365Ethyl SalicylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

H2SO4 (1.5 mL, 28.14 mmol) was added to a solution of salicylic acid (1.50 g, 10.860 mmol) in EtOH (50 mL). The reaction mixture was refluxed for 2 days, allowed to reach r.t., and it was diluted with CH2Cl2 (200 mL). The organic layer was washed with Na2CO3 (1 M aqueous solution, 200 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated to furnish 1.26 g of ethyl 2-hydroxybenzoate (yellow-coloured oil, yield: 70%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 days
  2. customto reach r.t.
  3. washThe organic layer was washed with Na2CO3 (1 M aqueous solution, 200 mL)
  4. dry with materialIt was dried over Na2SO4 (anhydrous)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e550bcad4a746b4b4a23b5ab5079348
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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