Acetone → Diacetone L-sorbose

HRID 358133

반응식

HRID 358133 반응식
[CH3:1][C:2]([CH3:4])=[O:3].O[CH2:6][C:7]([C@H:9]([C@@H:11]([C@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])=[O:8].I.N1C=C[CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1([CH3:4])[O:10][C@H:9]2[C@@H:11]3[O:12][C:20]([CH3:21])([CH3:19])[O:14][C@:13]3([CH2:15][OH:16])[O:8][C@H:7]2[CH2:6][O:3]1

참가 물질

5

반응물 4

HCID 180AcetoneHCID 1049PyridineHCID 6904L-(-)-SorboseHCID 24841Hydrogen iodide

생성물 1

HCID 11043496Diacetone L-sorbose수율 84%

반응 조건

온도
60 °C

실험 절차

To 200 ml of acetone were added 10.0 g of L-sorbose and 223 mg of hydriodic acid (57%) and the mixture was refluxed with stirring in a water bath at 60° C. for 6 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the cooling jacket. After completion of the reaction, a small amount of pyridine was added. The acetone was then distilled off under reduced pressure and the residue was dissolved in benzene. The benzene solution was washed with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. The benzene was distilled off under reduced pressure to give 12.13 g (84.0%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose (purity ≥98%). Melting point: 77°-78° C. (recrystallized from petroleum ether).

후처리

  1. temperaturethe mixture was refluxed
  2. customDuring this reaction
  3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
  4. customAfter completion of the reaction
  5. distillationThe acetone was then distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in benzene
  7. washThe benzene solution was washed with aqueous sodium bicarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe benzene was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-61169ec443be4360ba80f9006bf3a286
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04464530

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