Thionyl Chloride → 4'-Octyl-4-biphenylcarboxylic acid chloride
Reaktionsgleichung
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:26])=O>CN(C)C=O>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([Cl:26])=[O:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a round bottom flask of 100 ml was placed 1.5 g of 4'-octylbiphenyl-4-carboxylic acid, added 3 g of thionyl chloride, and further added a small amount of N,N-dimethyl formamide, and then the contents in the flask were subjected to reflux for 4 hours. An excess amount of thionyl chloride was distilled off to obtain 1.6 g of 4'-octylbiphenyl-4-carboxylic acid chloride. To this acid chloride was added a solution prepared by dissolving 0.6 g of optically active 4-hydroxy benzoic acid 2-octyl ester having an optical purity of 98% e.e., 0.4 g of triethylamine, and 0.15 g of dimethylamino pyridine in 50 ml of methylene chloride, and then the contents in the flask were stirred a whole day and night. After finishing the reaction, white insoluble matters produced were filtered off. After methylene chloride layer formed was washed sufficiently with a diluted hydrochloric acid and water, and dried, the organic solvent was separated under a reduced pressure. Crude products thus obtained were purified by column chromatography and recrystallization to obtain an objective compound having an optical purity of 98% e.e.
Aufarbeitung
- customTo a round bottom flask of 100 ml was placed
- temperatureto reflux for 4 hours
- distillationAn excess amount of thionyl chloride was distilled off
Quellen und Nachweise
- ORD-Eintrag
- ord-530fb8d389184df0b55b37dc53d15927
- Quelldatensatz
- uspto-grants-1995_02
- Patentnummer
- US05393460
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