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

HRID 2416364Notes

Reaction equation

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]

Participants

Conditions

Temperature: 24 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-6781369d6ad044c689417a2def9e6106
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06824709B2

Reaction notes

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