Toluene → 5,8-Dimethyl-2-naphthaldehyde
Reaktionsgleichung
ClC1[C:7](=[O:8])[C:6]([C:9]#N)=[C:5](C#N)[C:4](=O)C=1Cl.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCOC[CH2:23]1>>[CH3:21][C:15]1[CH:20]=[CH:19][C:18]([CH3:23])=[C:17]2[C:16]=1[CH:4]=[CH:5][C:6]([CH:7]=[O:8])=[CH:9]2Komponenten
4
Versuchsvorschrift
In a nitrogen atmosphere, the obtained aldehyde (20.9 g) was dissolved in dioxane (300 ml). After adding dichlorodicyanobenzoquinone (50.9 g), the resultant mixture was heated under ref lux for 1.5 hr. Then, it was cooled to room temperature by allowing to stand followed by the addition of toluene (500 ml). The resulting precipitate was collected by filtration and washed with toluene several times. The filtrate was concentrated and the resulting crude product was purified by silica gel column chromatography to give 5,8-dimethyl-2-naphtaldehyde (10.3 g) as colorless crystals.