1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 1-(Cycloocta-2,6-dienyloxy)-2,2,6,6-tetramethyl-4-hydroxypiperidine
Reaction equation
[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]1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
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.