(5-Carboxypentyl)triphenylphosphanium bromide → HCID 73753002, Verbindung

HRID 1383288

Reaktionsgleichung

Reaktionsgleichung von HRID 1383288
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[OH:29][CH:30]([CH3:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](=O)[CH3:38]>O1CCCC1>[OH:29][CH:30]([CH3:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([CH3:38])=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Komponenten

4

Edukt 2

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 211874079-Hydroxy-2-decanone

Produkt 1

HCID 73753002HCID 73753002, VerbindungAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

325 g (0.7 mol) of (5-carboxypentyl)triphenylphosphonium bromide were dissolved in 1500 ml of tetrahydrofuran. After the addition of 180 g (1.6 mol) of potassium t-butylate in 700 ml of tetrahydrofuran the mixture was treated with 175 g (0.71 mol) of 9-hydroxy-2-decanone (70% purity). After usual work up 186 g of crude 14-hydroxy-7-methyl-pentadec-6-enoic acid were obtained. This product was dissolved in 400 ml of methanol and, after the addition of 5 ml of concentrated sulphuric acid, heated to reflux for 2 hours. After work up, bulb-tube distillation and chromatography 102 g (50%) of methyl 14-hydroxy-7-methyl- pentadec-6-enoate were obtained having the following characteristics:

Quellen und Nachweise

ORD-Eintrag
ord-bc42591867964792bde017d4e9f14f30
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255276B1

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