Propanal → 2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal

HRID 15624

Reaktionsgleichung

[CH3:1][C:2]1[C:6]([CH3:8])([CH3:7])[CH:5]([CH2:9][CH:10]=O)[CH2:4][CH:3]=1.[CH:12](=[O:15])[CH2:13][CH3:14]>N1CCCCC1.C(O)(=O)C>[CH3:14][C:13](=[CH:10][CH2:9][CH:5]1[CH2:4][CH:3]=[C:2]([CH3:1])[C:6]1([CH3:7])[CH3:8])[CH:12]=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A 500 mL four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 171 g (0.98 mol) of campholenic aldehyde (purity: 88%), 3.8 g (0.045 mol) of piperidine and 2.8 g (0.046 mol) of acetic acid, and the contents in the flask were stirred while heating at 100° C. Then, 92 g (1.6 mol) of propionaldehyde was gradually dropped into the flask for 6 h, and the resultant mixture was aged for 1 h and then cooled. Thereafter, 3.2 g (0.053 mol) of acetic acid was added to the mixture to remove amines therefrom, thereby separating the mixture into two layers. The thus separated organic layer was washed with water and separated into two layers, thereby obtaining 279 g (0.79 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 54.7%) (yield based on theoretical amount: 81%).

Aufarbeitung

customA 500 mL four-necked flask equipped with a stirrer
temperaturecooled
customto remove amines
customseparating the mixture into two layers
washThe thus separated organic layer was washed with water
customseparated into two layers

Quellen und Nachweise

ORD-Eintrag: ord-6ed8be084f0a4aabb4f5884d78af949f
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732644B2

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