Carbon Dioxide → 9,9-Dioctyl-9H-fluorene-2-carboxylic Acid

HRID 917240

Reaktionsgleichung

Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=2[CH:3]=1.C([Li])CCC.[C:36](=[O:38])=[O:37].Cl>O1CCCC1>[CH2:23]([C:5]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]2[CH:3]=[C:2]([C:36]([OH:38])=[O:37])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

Into a flask fitted with a nitrogen inlet and rubber septum were introduced 2-bromo-9,9-dioctylfluorene (34.18 g, 72.8 mmole) and dry tetrahydrofuran (300 mL). The solution was cooled to −60° C. and n-butyl lithium (29.1 mL, 2.5M in hexanes, 72.8 mmole) added via a syringe. The reaction mixture was observed to turn red. After stirring for 1 hour at −60° C., the reaction mixture was poured onto powdered dry-ice and left to stand overnight. The mixture was acidified with 1M HCl and extracted with chloroform. The chloroform extract was washed with water, dried over magnesium sulfate and concentrated to give the acid as an oil.

Aufarbeitung

customInto a flask fitted with a nitrogen inlet
additionthe reaction mixture was poured
waitleft
waitto stand overnight
extractionextracted with chloroform
extractionThe chloroform extract
washwas washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-ae374cb4cd624c8caf93abecd566ff53
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07271406B2

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