Tetrahydrofuran → (2,6-dimethylphenyl)methanesulfonyl Chloride
Reaktionsgleichung
O1CCCC1.[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[CH2:14][S:15]([OH:18])(=O)=[O:16].C(Cl)(=O)C([Cl:22])=O>CN(C)C=O>[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[CH2:14][S:15]([Cl:22])(=[O:18])=[O:16]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
Tetrahydrofuran (3.0 L), (2,6-dimethyl-phenyl)-methanesulfonic acid (300 g, containing 12% water by KF analysis, or 266 g corrected for water content), and N,N-dimethylformamide (15 g) were combined in a 5 L multi-necked flask equipped with overhead stirring. The reaction mixture was cooled to −20° C. and oxalyl chloride (655.5 g) was added slowly over 1 h. The reaction mixture was clarified by filtration and concentrated to a volume of 1 L. The filtrate was transferred to a flask equipped with overhead stirring and cooled to −40° C. Water (900 mL) was added over 30 minutes, maintaining an internal temperature of <−10° C. The product was collected by filtration, washed with water and heptane, and dried to give (2,6-dimethyl-phenyl)-methanesulfonic chloride (277 g, 96%). 1H NMR (300 MHz, CDCl3): δ 7.25-7.04 (m, 3H, ArH), 5.17 (s, CH2), and 2.50 (s, 6H, CH3).
Aufarbeitung
- customequipped with overhead stirring
- filtrationThe reaction mixture was clarified by filtration
- concentrationconcentrated to a volume of 1 L
- customThe filtrate was transferred to a flask
- customequipped
- temperaturecooled to −40° C
- additionWater (900 mL) was added over 30 minutes
- temperaturemaintaining an internal temperature of <−10° C
- filtrationThe product was collected by filtration
- washwashed with water and heptane
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-1e158222fa9a483cb97cf444434baa39
- Quelldatensatz
- uspto-grants-2008_01
- Patentnummer
- US07321061B2
Notizen zur Reaktion
Wird geladen…