Hydrochloric Acid → Khellinone

HRID 894476

반응식

HRID 894476 반응식
[OH-].[K+].CC1[O:21][C:9]2[C:10]([O:19][CH3:20])=[C:11]3[O:18][CH:17]=[CH:16][C:12]3=[C:13]([O:14][CH3:15])[C:8]=2[C:6](=[O:7])[CH:5]=1.Cl>O>[CH3:5][C:6]([C:8]1[C:9]([OH:21])=[C:10]([O:19][CH3:20])[C:11]2[O:18][CH:17]=[CH:16][C:12]=2[C:13]=1[O:14][CH3:15])=[O:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3828Khellin3회HCID 14797Potassium Hydroxide

생성물 1

HCID 68086Khellinone수율 92.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of potassium hydroxide (193.2 g) in 1.5 l of water, heated to 75° C., is added 300 g of khellin (formula XXI) in 50 g portions over a period of 30 minutes. When khellin addition is complete, the resulting mixture is then heated to reflux for 2 hr and thereafter cooled to ambient temperature. Concentrated hydrochloric acid (300 ml) is then added to the cooled solution and the resulting precipitate is collected by filtration and dried at ambient temperature in a vacuum for 18 hr. The resulting crude yellow solid is then recrystallized from one liter of methanol, yielding 251 g of pure title product. Melting point is 99°-100° C. Silica gel TLC Rf is 0.60 is hexane and ethyl acetate (1:1). Infrared absorptions are observed at 3160, 3140, 1700, 1695, 1680, 1620, 1590, 1550, 1300, 1265, 1150, 1075, and 1060 cm-1. NMR absorptions are observed at 7.52, 6.91, 4.15, 4.05, 2.72, and 13.06δ (deuterochloroform solvent). The mass spectrum exhibits peaks at 236, 221, 206, 203, 191, 175, 163, and 119. Carbon:hydrogen ratio is 60.65:5.15.

후처리

  1. temperaturethe resulting mixture is then heated
  2. temperatureto reflux for 2 hr
  3. filtrationthe resulting precipitate is collected by filtration
  4. customdried at ambient temperature in a vacuum for 18 hr
  5. customThe resulting crude yellow solid is then recrystallized from one liter of methanol

출처 및 근거

ORD 기록
ord-cc7ba737b5c349f0a8c3ff93d874aaa1
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284569

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