Hydrochloric Acid → Khellinone

HRID 1278262

反応式

HRID 1278262 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3828Khellin3 回HCID 14797Potassium Hydroxide

生成物 1

HCID 68086Khellinone収率 92.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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 in hexane and ethyl acetate (1:1). Infrared absorptions are observed at 3160, 3140, 2700, 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.

後処理

  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

出典と根拠

ORDレコード
ord-d5a1f3c1fe4f40f7854ef91f9b8a8393
出典データセット
uspto-grants-1981_07
特許番号
US04281013

関連ノート

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