Imidazole → 5-Ethenyl-2-methoxyphenol

HRID 2357423Notes

Reaction equation

HRID 2357423 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.[C:15]([O-])([O-])=O.[K+].[K+].N1C=CN=C1>CN(C)C=O>[CH:3]([C:4]1[CH:5]=[C:6]([OH:7])[C:9]([O:10][CH3:15])=[CH:11][CH:12]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 445858Ferulic Acid

Product 1

HCID 104418575-Ethenyl-2-methoxyphenolYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Ferulic acid (0.0083 mol), K2CO3 (10%, 3 ml), imidazole (1 mL) and dimethylformamide (15 ml) were taken in a 250 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well and placed inside the microwave oven over an ice bath and irradiated for 30 minutes in parts. After completion of reaction, it was worked up and purified as in example V and provided sweet and pleasant smelling viscous liquid. 59% yield; (Spectral data as in example V)

Workup

  1. customfitted with a loose funnel at the top
  2. customplaced inside the microwave oven over an ice bath
  3. customirradiated for 30 minutes in parts
  4. customAfter completion of reaction, it
  5. custompurified as in example V
  6. customprovided sweet

Sources & evidence

ORD record
ord-21b7353b9fd14b59afa306d8c6c09164
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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