Ethanol → Ethyl homovanillate

HRID 2092401Notes

Reaction equation

HRID 2092401 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.OS(O)(=O)=O.[CH3:19][CH2:20]O>>[CH2:19]([O:12][C:1](=[O:13])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1738Homovanillic Acid

Product 1

HCID 108965Ethyl homovanillate

Conditions

Temperature
85 °C

Procedure

A mixture of homovanillic acid (5 g, 27.4 mmol) and H2SO4 (96%, 1.46 mL, 27.4 mmol) in EtOH (100 mL) was stirred for 1 h at 85° C., allowed to cool to RT and concentrated. The residue was diluted in H2O and extracted with DCM. The organic phase was washed with H2O, dried (Na2SO4), filtered and concentrated to afford 5.8 g of the title compounds as a yellow oil. LC-MS: m/z 211.2 [M+H]+.

Workup

  1. temperatureto cool to RT
  2. concentrationconcentrated
  3. additionThe residue was diluted in H2O
  4. extractionextracted with DCM
  5. washThe organic phase was washed with H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-18c6ca74cde142128b7c2aebd19ed90d
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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