1-(2,2-Diethoxyethoxy)-4-methoxybenzene → Acetaldehyde, (4-methoxyphenoxy)-

HRID 500139Notes

Reaction equation

HRID 500139 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)C>Cl.CC(C)=O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]=[O:3])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 2513151-(2,2-Diethoxyethoxy)-4-methoxybenzene

Product 1

HCID 96383Acetaldehyde, (4-methoxyphenoxy)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

1-(2,2-Diethoxyethoxy)-4-methoxybenzene (4.8 g, 20 mmol) was dissolved in 1% aqueous HCl (30 mL) and acetone (15 mL). The reaction mixture was heated under refluxed for 2 h. Acetone was removed under reduced pressure. The aqueous mixture was neutralized with saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was dried under reduced pressure to afford the desired product which was used in the next step without further purification. (3.30 g, 99.3%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder refluxed for 2 h
  3. customAcetone was removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-e2660e9e302d4e51a4b28efbed951e84
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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