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

HRID 15619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 15619
[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)CCCCCCCCCCCCCCCCC.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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 527PropanalHCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

Produkt 1

HCID 30175572-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enalAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 5281Stearic AcidKatalysator
HCID 8082
Piperidine
Katalysator

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 13.1 g (0.046 mol) of stearic acid, and the contents in the flask were stirred while heating at 100° C. Then, 91 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 295 g (0.93 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 60.6%) (yield based on theoretical amount: 95%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5d449bcf8e7f4469af6a74da47b5a3ab
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07732644B2

Notizen zur Reaktion

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