Acetic Acid → 5-(Phenylethynyl)adamantane-1,3-dicarboxylic acid

HRID 2195586

Reaktionsgleichung

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ON1C(=O)C2=CC=CC=C2[C:13]1=[O:22].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[CH:24].[C]=[O:32].O=O.Cl.[C:36]([OH:39])(=[O:38])C>C/C(/O)=C\C(C)=O.C/C(/O)=C/C(C)=O.[Co]>[C:25]1([C:23]#[C:24][C:1]23[CH2:10][C:5]4([C:36]([OH:39])=[O:38])[CH2:6][CH:7]([CH2:9][C:3]([C:13]([OH:22])=[O:32])([CH2:4]4)[CH2:2]2)[CH2:8]3)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Under the atmosphere of nitrogen gas, 10 g (73 mmole) of adamantane, 1.2 g (7.4 mmole) of N-hydroxyphthalimide, 80 mg (0.31 mmole) of cobalt(II) acetylacetonate, 9.2 g (90 mmole) of ethynylbenzene and 150 ml of acetic acid were stirred. To the resultant mixture, a mixed gas containing 2.0 liters of carbon monoxide and 0.50 liters of oxygen was introduced under a pressure of 7.5 kg/cm2, and the mixture was stirred at 60° C. for 12 hours. The reaction fluid was added into a 5 mole/liter aqueous solution of hydrochloric acid cooled at 0° C., and the solid substance was recovered by filtration. The obtained solid substance was purified in accordance with the liquid chromatography and recrystallization, and 5-(phenylethynyl)adamantane-1,3-dicarboxylic acid was obtained.

Aufarbeitung

additionwas introduced under a pressure of 7.5 kg/cm2
temperaturecooled at 0° C.
filtrationthe solid substance was recovered by filtration
customThe obtained solid substance was purified in accordance with the liquid chromatography and recrystallization

Quellen und Nachweise

ORD-Eintrag: ord-f8a3bcfa73ae440ebb5367a96e769620
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08337982B2

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