Hydrogen Peroxide → 2,7-Diacetyloxy-9-methylfluorene

HRID 2416364ノート

反応式

HRID 2416364 の反応式
S(=O)(=O)(O)O.C([C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15](C(=O)C)=[CH:16][CH:17]=3)[CH:12]([CH3:25])[C:11]=2[CH:10]=1)(=O)C.C([O:29][C:30](=[O:32])[CH3:31])(=O)C.OO>O.ClCCl>[C:30]([O:32][C:16]1[CH:15]=[CH:14][C:13]2[C:12]3[C:11](=[CH:10][C:9]([O:29][C:30](=[O:32])[CH3:31])=[CH:21][CH:25]=3)[CH:19]([CH3:20])[C:18]=2[CH:17]=1)(=[O:29])[CH3:31]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 226302652,7-Diacetyl-9-methylfluorene

生成物 1

HCID 226302552,7-Diacetyloxy-9-methylfluorene収率 36.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
24 °C

実験手順

36M-sulfuric acid (12 mL) was slowly dropwise added to a mixture of 2,7-diacetyl-9-methylfluorene (30 g), dichloromethane (30 mL), acetic anhydride (35 g) and a 34% hydrogen peroxide aqueous solution (34.6 g) while maintaining 3° C. or lower. The resulting mixture was stirred at 24° C. for 7 hours and then poured into water. The separated organic layer was sufficiently washed in order with saturated sodium hydrogencarbonate, 10% saturated sodium hydrogensulfite and water, and then dried on anhydrous magnesium sulfate. The solvent was distilled off from this organic layer under reduced pressure, and the resulting residue was purified by means of column chromatography (silica gel, eluting solvent: heptane/toluene [6/4]) and recrystallization (ethanol) to obtain 2,7-diacetyloxy-9-methylfluorene (12.4 g) of colorless crystal. Melting point: 138.6-139.7° C.

後処理

  1. washThe separated organic layer was sufficiently washed in order with saturated sodium hydrogencarbonate, 10% saturated sodium hydrogensulfite and water
  2. dry with materialdried on anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off from this organic layer under reduced pressure
  4. customthe resulting residue was purified by means of column chromatography (silica gel, eluting solvent: heptane/toluene [6/4]) and recrystallization (ethanol)

出典と根拠

ORDレコード
ord-6781369d6ad044c689417a2def9e6106
出典データセット
uspto-grants-2004_11
特許番号
US06824709B2

反応ノート

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