Water → 2-Methyl-5-phenylpyridine

A suspension of 100 g of wet Raney Nickel in 1.5 L of dodecanol in a three-neck round bottom flask equipped with a Dean Stark apparatus was heated until the temperature reached 130° C., then 3-phenylpyridine (Aldrich) was added and the reaction was heated at 190°-200° C. for 6 hours. During the reaction, H2O was constantly eliminated. When the reaction was over, half of the dodecanol was removed by distillation. After cooling the reaction mixture to room temperature, 200 mL of H2O and 400 mL of hexane were added, the mixture was shaken, and the hexane layer decanted. This process was repeated several times. The combined hexane fractions were washed with 1N HCl until the disappearance of 5-phenyl-2-picoline from the organic phase. The combined aqueous layers were filtered, washed with hexane, basified with 10N NaOH, and extracted with CH2Cl2. The organic layer was washed with NH4OAc (25%), dried over MgSO4, and evaporated to dryness. The crude residue was then distilled under vacuum (100° C. at 0.1 mm of Hg) to afford the pure title product.

1. customequipped with a Dean Stark apparatus
2. temperaturewas heated until the temperature
3. customreached 130° C.
4. temperaturethe reaction was heated at 190°-200° C. for 6 hours
5. customwas removed by distillation
6. addition200 mL of H2O and 400 mL of hexane were added
7. customthe hexane layer decanted
8. washThe combined hexane fractions were washed with 1N HCl until the disappearance of 5-phenyl-2-picoline from the organic phase
9. filtrationThe combined aqueous layers were filtered
10. washwashed with hexane
11. extractionextracted with CH2Cl2
12. washThe organic layer was washed with NH4OAc (25%)
13. dry with materialdried over MgSO4
14. customevaporated to dryness
15. distillationThe crude residue was then distilled under vacuum (100° C. at 0.1 mm of Hg)

ORD-Eintrag

ord-61dcb9b628224b458cbab05fe01eedcd

Quelldatensatz

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05314900