Ethanol → Ethyl homovanillate

HRID 2221620Notes

Reaction equation

HRID 2221620 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:19][CH3:20])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1738Homovanillic Acid

Product 1

HCID 108965Ethyl homovanillateYield 90%

Procedure

A mixture of (4-hydroxy-3-methoxyphenyl)acetic acid (15.00 g), conc. sulfuric acid (5 mL) and anhydrous ethanol (100 mL) was heated under reflux for 17 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:9 to 7:3, v/v) to give ethyl (4-hydroxy-3-methoxyphenyl)acetate as a colorless oil (14.55 g, yield 90%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hrs
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed successively with distilled water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:9 to 7:3

Sources & evidence

ORD record
ord-ba4b6024b6de4cafa7552a1bdc46b5dc
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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