D-Glucose → p-Isobutylpropiophenone dimethyl ketal

HRID 903111

반응식

HRID 903111 반응식
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].O[CH:22]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>CO>[CH3:22][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]

참가 물질

5

반응물 3

HCID 5793D-GlucoseHCID 1088341-(4-(2-Methylpropyl)phenyl)-1-propanoneHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)

생성물 1

HCID 13298986p-Isobutylpropiophenone dimethyl ketal

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To 11.33 g. (0.10 mole) of methyl acetimidate hydrochloride, prepared by known procedures, in a 100 ml. 3-necked, round-bottomed 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.

후처리

  1. addition3-necked, round-bottomed 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

출처 및 근거

ORD 기록
ord-675b331c6e4642918b98d571314f21c0
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04226790

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