2-Methylimidazole → HCID 277395, compound

HRID 2357418Notes

Reaction equation

HRID 2357418 reaction equation
[C:1]1([C:7](=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].CC1NC=CN=1>O>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 516892Sodium BicarbonateHCID 53411296α-[(4-Hydroxy-3-methoxyphenyl)methylene]benzeneacetic acid

Product 1

HCID 277395HCID 277395, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of α-phenyl-4-hydroxy-3-methoxy cinnamic acid (0.0083 mol), NaHCO3 (10%, 5 mL), methylimidazole (2 mL) and polyethylene glycol (5 mL) were taken in a 100 ml round bottom flask fitted with a condenser. The flask was shaken well and placed inside the microwave oven and irradiated (200 W, 180° C.) for 10 minutes in parts. After completion of reaction, water added to the reaction mixture and solid precipitate formed were filtered and washed with water to obtain pure product (yield 96%) in most of the cases or further purified in silica-gel column with ethylacetate and hexane (40-60%); solid, (m.p. 132-134° C.); 1H NMR (CDCl3) δ 7.45 (2H, d, J=7.41 Hz), 7.32 (2H, m), 7.21 (1H, m), 7.02 (5H, m), 5.66 (1H, s), 3.89 (3H, s); 13C NMR (CDCl3) δ 146.7, 145.6, 137.6, 130.0, 128.7, 127.2, 126.5, 126.2, 120.5, 114.6, 108.3 and 55.9. HREIMS data: m/z [M+H]+ for C15H15O2, calculated=227.2840; observed=227.2826.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted with a condenser
  3. customirradiated (200 W, 180° C.) for 10 minutes in parts
  4. additionadded to the reaction mixture and solid precipitate
  5. customformed
  6. filtrationwere filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-83205574316e4e00998ce4f9c5c772e6
Source dataset
uspto-grants-2010_07
Patent number
US07759527B2

Reaction notes

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