Hydrochloric Acid → (2,6-Dimethylphenyl)acetaldehyde

HRID 539490Notes

Reaction equation

HRID 539490 reaction equation
Cl.O.C[O:4][CH:5]=[CH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:14]>O1CCOCC1>[CH3:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:7]=1[CH2:6][CH:5]=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 70654520HCID 70654520, compound

Product 1

HCID 53403477(2,6-Dimethylphenyl)acetaldehydeYield 86.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Concentrated HCl (35 mL, 420 mmol) was slowly added to water (55 mL) and then 2-(2-methoxyvinyl)-1,3-dimethylbenzene (11.2 g, 69.0 mmol) in dioxane (35 mL) was added in one portion. The biphasic mixture was heated to reflux for 16 h, cooled to room temperature and extracted with ethyl acetate (3×100 mL). After drying over sodium sulfate, filtering and removing the solvent under reduced pressure, the crude material was purified by bulb-to-bulb distillation (100° C., 93 mbar) to give 8.8 g (86%) of 2-(2,6-dimethylphenyl)acetaldehyde as a white solid. The product was confirmed by GC/MS and NMR.

Workup

  1. temperatureThe biphasic mixture was heated
  2. temperatureto reflux for 16 h
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialAfter drying over sodium sulfate
  5. filtrationfiltering
  6. customremoving the solvent under reduced pressure
  7. distillationthe crude material was purified by bulb-to-bulb distillation (100° C., 93 mbar)

Sources & evidence

ORD record
ord-10007e7f23fd4361a4ae55d48638e7d2
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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