Ethanol → Ethyl (3-Hydroxyphenyl)acetate

HRID 1873642Notes

Reaction equation

HRID 1873642 reaction equation
OS(O)(=O)=O.[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.[CH3:17][CH2:18]O>>[CH2:17]([O:15][C:14](=[O:16])[CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([OH:6])[CH:8]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 572437Ethyl (3-Hydroxyphenyl)acetateYield 96%

Procedure

Concentrated H2SO4 (2 mL, 36 mmol) was added to a suspension of 3-hydroxyphenylacetic acid (25.9 g, 170 mmol) in EtOH (340 mL). The reaction mixture was heated at reflux for 4 hours then cooled to room temperature. The volatiles were removed in vacuo and the residue was suspended in EtOAc (300 mL). The organic layer was washed with saturated aqueous NaHCO3 (1×150 mL), brine (1×150 mL), dried (anhydrous MgSO4), and concentrated under reduced pressure to give the ester as a colorless oil (29.3 g, 96% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customThe volatiles were removed in vacuo
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (1×150 mL), brine (1×150 mL)
  5. dry with materialdried (anhydrous MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4707506caed14d1e842d9b6e82a14f3a
Source dataset
uspto-grants-2012_11
Patent number
US08304418B2

Reaction notes

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