Methanol → p-Isobutylpropiophenone dimethyl ketal

HRID 1391360Notes

Reaction equation

HRID 1391360 reaction equation
Cl.[C:2](=N)([O:4]C)C.[CH2:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9].[CH3:21]O>>[CH3:21][O:20][C:17]([O:4][CH3:2])([C:14]1[CH:13]=[CH:12][C:11]([CH2:7][CH:8]([CH3:10])[CH3:9])=[CH:16][CH:15]=1)[CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 1088341-(4-(2-Methylpropyl)phenyl)-1-propanoneHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)

Product 1

HCID 13298986p-Isobutylpropiophenone dimethyl ketal

Procedure

To 11.33 g. (0.10 mole) of methyl acetimidate hydrochloride, prepared by known methods, in a 100 ml. 3-necked, round bottom flask there was added a solution of 9.71 g. (actual 9.42 g.; 49.6 mmole) of crude p-isobutylpropiophenone, prepared as described in part A above, in 23 ml. of absolute methanol. The resulting solution was stirred for 12 hours at room temperature to insure complete reaction. Gas liquid chromatographic analysis (GLC analysis) of an aliquot of the reaction mixture indicated greater than 99% ketal formation. The resulting mixture was filtered to remove the precipitated ammonium chloride and concentrated under vacuum. Hexane (50 ml.) was added to the residue and the resulting solution was again filtered to remove any acetamide which might be present. Removal of the hexane solvent under vacuum gave p-isobutylpropiophenone dimethyl ketal as a pale yellow oil which was used without further purification. The NMR was in accord.

Workup

  1. addition3-necked, round bottom flask there was added a solution of 9.71 g
  2. customreaction
  3. filtrationThe resulting mixture was filtered
  4. customto remove the precipitated ammonium chloride
  5. concentrationconcentrated under vacuum
  6. additionHexane (50 ml.) was added to the residue
  7. filtrationthe resulting solution was again filtered
  8. customto remove any acetamide which
  9. customRemoval of the hexane solvent under vacuum

Sources & evidence

ORD record
ord-99c328114f034f5e84c2b016ac8620e6
Source dataset
uspto-grants-1979_02
Patent number
US04142054

Reaction notes

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