Ethylene Glycol → HCID 66811313, compound

HRID 1097821Notes

Reaction equation

HRID 1097821 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:25](O)[CH2:26][OH:27]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]1[O:27][CH2:26][CH2:25][O:6]1

Participants

5

Reactant 3

HCID 174Ethylene Glycol2×HCID 6101p-Toluenesulfonic acid2×HCID 27595992-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 66811313HCID 66811313, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-methoxy-4-nitro-benzaldehyde (4.61 g, 25.4 mmol) in toluene (51 mL), was added p-toluene sulfonic acid (483 mg, 2.54 mmol), followed by ethylene glycol (2.83 mL, 50.8 mmol). After heating the reaction mixture at 50° C. for 12 h, additional p-toluene sulfonic acid (483 mg, 2.54 mmol) and ethylene glycol (2.83 mL, 50.8 mmol) were added. After an additional 12 h, the solvent was removed under reduced pressure, and the resulting residue was dissolved in dichloromethane (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (25 mL), dried over sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound as a yellow solid (5.46 g, 95%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in dichloromethane (50 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (25 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-74d9449ac29945e09d4576311b984917
Source dataset
uspto-grants-2012_03
Patent number
US08143277B2

Reaction notes

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