2-Methylimidazole → 5-Ethenyl-2-methoxyphenol

HRID 2357422Notes

Reaction equation

HRID 2357422 reaction equation
C(O)(=O)/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7]C)[CH:5]=1.[OH-].[K+].[CH3:17]C1NC=CN=1>CN(C)C=O>[CH:3]([C:4]1[CH:5]=[C:6]([OH:7])[C:9]([O:10][CH3:17])=[CH:11][CH:12]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 14797Potassium HydroxideHCID 445858Ferulic Acid

Product 1

HCID 104418575-Ethenyl-2-methoxyphenolYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Ferulic acid (0.0083 mol), KOH (10%, 3 ml), methylimidazole (1 mL) and dimethylformamide (10 ml) were taken in a 100 ml round bottom flask fitted with reflux condenser. The flask was placed inside the microwave oven and irradiated (150 W, 150° C.) for 12 minutes. The cooled mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl, water, saturated sodium bicarbonate, brine and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel column chromatography using mixture of hexane and ethyl acetate (9:1 to 6:4), provided sweet and pleasant smelling viscous liquid. 64% yield; 1H NMR (CDCl3) δ 6.90 (3H, m), 6.70 (1H, dd, J=10.90 Hz and J=17.36 Hz), 5.79 (1H, s), 5.59 (1H, d, J=17.36 Hz), 5.11 (1H, d, J=10.90 Hz), 3.83 (3H, s); 13C NMR (CDCl3) δ 146.7, 145.7, 136.7, 130.3, 120.1, 114.5, 111.4, 108.1, 55.9.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted
  3. temperaturewith reflux condenser
  4. customirradiated (150 W, 150° C.) for 12 minutes
  5. additionThe cooled mixture was poured into ice-cold water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with dil HCl, water, saturated sodium bicarbonate, brine
  8. dry with materialorganic layer dried over sodium sulphate
  9. customThe solvent was evaporated under reduced pressure
  10. customto obtain liquid which
  11. customwas purified on silica gel column chromatography
  12. additionmixture of hexane and ethyl acetate (9:1 to 6:4)
  13. customprovided sweet

Sources & evidence

ORD record
ord-50e6d06317ae4f0c810f0bcbb4499626
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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