Thionyl Chloride → HCID 54421434, Verbindung
Reaktionsgleichung
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.S(Cl)(Cl)=O.[CH3:24][C@@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26]O>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([O:19][CH2:24][C@@H:25]([CH3:26])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1Komponenten
Versuchsvorschrift
4'-Acetoxybiphenyl-4-carboxylic acid (5.80 g) was converted to an acid chloride using thionyl chloride, and the acid chloride was reacted with (S)-2-methyloctanol. The reaction mixture was extracted with diethyl ether, and the ethereal layer was thoroughly dried. Benzylamine was added thereto in small portions at room temperature. Hydrochloric acid was further added thereto, and the mixture was washed with water. The solvent was removed from the reaction mixture by distillation, and the resulting crude product was decolored by passing through a silica gel column (solvent: n-hexane-ethyl acetate mixture) and recrystallized from n-hexane to obtain 6.2 g of (S)-2-methyloctyl 4'-hydroxybiphenyl-4-carboxylate as white crystals having a melting point of 89° C.
Aufarbeitung
- extractionThe reaction mixture was extracted with diethyl ether
- customthe ethereal layer was thoroughly dried
- additionBenzylamine was added
- customat room temperature
- additionHydrochloric acid was further added
- washthe mixture was washed with water
- customThe solvent was removed from the reaction mixture by distillation
- customrecrystallized from n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-5fa92c9b6fb547b3a0e5f9c727a88503
- Quelldatensatz
- uspto-grants-1994_06
- Patentnummer
- US05324451
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