Ethylene Glycol → HCID 59660700, compound

HRID 1641430Notes

Reaction equation

HRID 1641430 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH:15]=[O:16])[CH:11]=[N:10]2)=[CH:5][CH:4]=1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:12]1[CH:11]=[N:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 27797351-(4-Methoxyphenyl)-5-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 59660700HCID 59660700, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methoxy-phenyl)-5-methyl-1H-pyrazole-4-carbaldehyde (0.5 g, 2.3 mmol), ethylene glycol (1.44 g, 23.1 mmol) and p-toluenesulfonic acid (0.2 g, 1.2 mmol) in toluene (10 mL) was refluxed for 18 h (Dean Stock to remove water formed). After it was allowed to cool to room temperature, the reaction mixture was diluted with ethyl acetate, washed with sat. NaHCO3 (aq) and brine, and dried over Na2SO4. After concentrated, the residue was purified by a column chromatography on silica gel to yield the title compound (0.35 g, 58%); MS (APCI) m/z: 261 (M+1, 80).

Workup

  1. temperaturewas refluxed for 18 h
  2. custom(Dean Stock to remove water formed)
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with sat. NaHCO3 (aq) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-a6db0c52a4614a47882bc7d6906dede7
Source dataset
uspto-grants-2012_02
Patent number
US08115005B2

Reaction notes

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