Sodium Hydroxide → 2-chloro-6-(3,5,5-trimethylhexyloxy)pyridine N-oxide

HRID 21692

Reaktionsgleichung

Reaktionsgleichung von HRID 21692
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N+:3]=1[O-:9].[CH3:10][CH:11]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13][OH:14].[OH-].[Na+]>CS(C)=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:14][CH2:13][CH2:12][CH:11]([CH3:10])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N+:3]=1[O-:9]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 189383,5,5-Trimethyl-1-hexanolHCID 8176732,6-Dichloropyridine N-Oxide

Produkt 1

HCID 538248392-chloro-6-(3,5,5-trimethylhexyloxy)pyridine N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The 0.82 g (0.0050 moles) of 2,6-dichloropyridine N-oxide and 0.80 g (90%) (0.0050 moles) of 3,5,5-trimethyl-1-hexanol was reacted with 0.206 g (0.0050 moles) of ground sodium hydroxide in 8.2 ml of DMSO at 80° C. for 8.5 hours to give 2-chloro-6-(3,5,5trimethylhexyloxy)pyridine N-oxide. It was reacted with 0.600 g (0.015 moles) of ground sodium hydroxide at 80° C. for 4 hours to give 1-hydroxy-6-(3,5,5-trimethyl-hexyloxy) pyridine-2(1H)-one. After cooling, it was added 74 ml of water and was adjusted with 6N HCL to pH 3. The precipitate was filtered and washed with water to give 0.577 g (45%). It was recrystallized from ethyl acetate and hexanes: mp 130.5°-131° C.

Quellen und Nachweise

ORD-Eintrag
ord-bf365ee63a3141adbc949b17123d9b8b
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424435

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