Toluene → HCID 66961793, compound

HRID 2247555Notes

Reaction equation

HRID 2247555 reaction equation
[C:1]1([CH3:7])C=CC=CC=1.[N:8]1([C:13]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:14]=2C=O)[CH:12]=[CH:11][N:10]=[CH:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[C:36](=O)([OH:38])[O-:37].[Na+]>C(OCC)(=O)C.C(O)CO>[O:37]1[CH2:7][CH2:1][O:38][CH:36]1[C:18]1[CH:17]=[CH:14][C:13]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[C:20]([O:21][CH3:22])[CH:19]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86585896Sodium bicarbonate waterHCID 86602483HCID 86602483, compound

Product 1

HCID 66961793HCID 66961793, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a toluene (70 mL) solution of 4-(1H-imidazol-1-yl-3-methoxybenzaldehyde (4.3 g) and ethylene glycol (6.5 g), para-toluenesulfonic acid monohydrate (4.8 g) was added, Dean-Stark equipment was attached and heat-refluxing was carried out for 4 hours. After allowing cool the reaction mixture to room temperature, a saturated sodium bicarbonate water and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with a saturated salt solution and concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), and 3.15 g of the title compound was obtained.

Workup

  1. temperatureheat-refluxing
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with a saturated salt solution
  4. concentrationconcentrated under reduced pressure
  5. dry with materialafter dried over anhydrous magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-c65fb672c4fb4203aad9564d2dea1c0d
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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