2-Methylimidazole → 3,4-Dimethoxystyrene

HRID 2357427Notes

Reaction equation

HRID 2357427 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7]C(O)=O.[OH-].[K+].CC1NC=CN=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH2:7]

Participants

4

Reactant 3

HCID 127492-MethylimidazoleHCID 14797Potassium HydroxideHCID 168483',4'-Dimethoxycinnamic acid

Product 1

HCID 614003,4-Dimethoxystyrene

Procedure

A mixture of 3,4-dimethoxycinnamic acid (0.0083 mol), KOH (10%, 5 ml), methylimidazole (1 mL) and polyethylene glycol (5 ml) were taken in a 100 ml round bottom flask fitted with reflux condenser. The flask was placed inside the microwave oven and irradiated (200 W, 200° C.) for 15 minutes. After completion of reaction, it was worked up and purified as in example V and provided a solid (m.p. 110-114° C.); 1H NMR (CDCl3) δ 7.01 (2H, m), 6.84 (1H, d, J=7.27 Hz), 6.63 (1H, d, J=10.80 Hz and J=16.10 Hz), 5.60 (1H, d, J=16.10 Hz), 5.15 (1H, d, J=10.80 Hz), 3.90 (1H, s), 3.87 (1H, s); 13C NMR (CDCl3) δ 150.1, 149.2, 137.4, 131.2, 119.8, 112.6, 111.6, 109.7 and 55.8.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted
  3. temperaturewith reflux condenser
  4. customirradiated (200 W, 200° C.) for 15 minutes
  5. customAfter completion of reaction, it
  6. custompurified as in example V

Sources & evidence

ORD record
ord-aaf4de9e1e974b2f8c3840e1ebddb51d
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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