1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 1-(Cycloocta-2,6-dienyloxy)-2,2,6,6-tetramethyl-4-hydroxypiperidine

HRID 322804

Reaktionsgleichung

Reaktionsgleichung von HRID 322804
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[CH:13]1[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16][CH2:15][CH:14]=1>>[CH:20]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:19][CH:18]=[CH:17][CH2:16][CH2:15][CH:14]=[CH:13]1

Komponenten

3

Edukt 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8135cis,cis-1,5-Cyclooctadiene

Produkt 1

HCID 702405201-(Cycloocta-2,6-dienyloxy)-2,2,6,6-tetramethyl-4-hydroxypiperidineAusbeute 33 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 29.4 g (0.17 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 148.0 g (1.37 mol) of 1,5-cyclooctadiene is heated under a nitrogen atmosphere at 100° C. for 24 hours. The reaction mixture is filtered to remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, and the filtrate is diluted with heptane (250 mL). The organic phase is washed with 5% ascorbic acid (2×50 mL) and distilled water (2×50 mL). The organic phase is dried over anhydrous magnesium sulfate and the volatiles removed in vacuo. The residue is chromatographed to give 8.1 g (33% yield) of the title compound as a white solid.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. customto remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine
  3. additionthe filtrate is diluted with heptane (250 mL)
  4. washThe organic phase is washed with 5% ascorbic acid (2×50 mL)
  5. distillationdistilled water (2×50 mL)
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. customthe volatiles removed in vacuo
  8. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-72a4d00cc3ca48cf9cad41f1c627458b
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211378B1

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