8-Hydroxy-6-methyl-2-octanone → 14-Hydroxy-8,12-dimethyltetradec-7-enoic acid

HRID 1383278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383278
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[OH:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][C:37](=O)[CH3:38]>O1CCCC1>[OH:30][CH2:31][CH2:32][CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][C:37]([CH3:38])=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Komponenten

4

Edukt 2

HCID 98152698-Hydroxy-6-methyl-2-octanoneHCID 11027094(6-Carboxyhexyl)triphenylphosphonium bromide

Produkt 1

HCID 7375300414-Hydroxy-8,12-dimethyltetradec-7-enoic acidAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

95 g (0.2 mol) of (6-carboxyhexyl)triphenylphosphonium bromide in 600 ml of tetrahydrofuran were added to 48 g (0.42 mol) of potassium t-butylate in 200 ml of tetrahydrofuran. Thereafter, 29 g (0.18 mol) of 8-hydroxy-6-methyl-2-octanone were added. After work up and chromatography 26 g (48%) of 14-hydroxy-8,12-dimethyltetradec-7-enoic acid were obtained having the following characteristics: Z/E=58/42;

Quellen und Nachweise

ORD-Eintrag
ord-d809ceb78d584b6f8f6d8126318032d7
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255276B1

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