Reaktionsgleichung
[O:1]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:18].[CH3:19][N:20](C)[OH:21].[CH3:23][Al](C)C>>[CH3:23][O:21][N:20]([CH3:19])[C:2](=[O:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:1]Komponenten
Versuchsvorschrift
More specifically, compound (I) where R1, R3, R4, R5 are methyl groups, R2 is a hydroxyl group, m=1 and n=13 can be prepared in the following manner: Oxacycloheptadecan-2-one reacts with dimethylhydroxylamine in the presence of trimethylaluminium at 0° C. and at atmospheric pressure to yield N-methoxy-N-methyl-16-hydroxyhexadecanamide. The hydroxy function of this compound is then protected in the presence of sodium hydride and benzyl bromide at −78° C. and atmospheric pressure. The resulting N-methoxy-N-methyl-16-benzyloxyhexadecanamide is subsequently treated with methyllithium at −78° C. and at atmospheric pressure to yield 17-benzyloxyheptadecan-2-one. This reacts with the vinylmagnesium to afford 18-benzyloxy-3-methyloctadec-1-en-3-ol that in the presence of trimethylhydroquinone, zinc chloride and concentrated hydrochloric acid yields 2-(15-benzyloxypentadecyl)-2,5,7,8-tetramethylchroman-6-ol. Catalytic hydrogenation of this compound in the presence of palladium on charcoal affords 2-(15-hydroxypentadecyl)-2,5,7,8-tetramethylchroman-6-ol.
Aufarbeitung
- customcan be prepared in the following manner
Quellen und Nachweise
- ORD-Eintrag
- ord-3c41ffd8a0e847d0a88a4e1f27f093af
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07691900B2
Verknüpfte Notizen
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