Ethylene Glycol → HCID 22722113, compound

HRID 1581652Notes

Reaction equation

HRID 1581652 reaction equation
[CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:6]=1[O:13][CH3:14].[CH2:17](O)[CH2:18][OH:19]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[C:9]([CH:11]2[O:19][CH2:18][CH2:17][O:12]2)[CH:8]=[CH:7][C:6]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 22722115HCID 22722115, compound

Product 1

HCID 22722113HCID 22722113, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

N-Methoxy-N-methyl-5-formyl-2-methoxybenzamide (6.56 g, 29.4 mnmol), ethylene glycol (8.20 mL, 147 mmol), p-toluenesulfonic acid monohydrate (110 mg, 0.578 mmol) and toluene (100 mL) were mixed, and, while removing water generated using dean-stark apparatus, the mixture was refluxed for 4 hours. After allowed to stand for cooling, ethyl acetate was added, which was washed with saturated aqueous solution of sodium hydrogencarbonate and water in sequence. Then, the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v) to obtain 6.60 g (84%) of the title compound as a colorless oil.

Workup

  1. customwhile removing water
  2. temperaturethe mixture was refluxed for 4 hours
  3. temperaturefor cooling
  4. additionethyl acetate was added
  5. washwhich was washed with saturated aqueous solution of sodium hydrogencarbonate and water in sequence
  6. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v)

Sources & evidence

ORD record
ord-41a7ca1dbb854c5b8aa6831f4d5ecb9b
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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