Toluene → 5,8-Dimethyl-2-naphthaldehyde
Reaction equation
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]2Participants
4
Procedure
20.9 g of the aldehyde compound was dissolved in 300 ml dioxane in a nitrogen atmosphere, then 50.9 g of dichlorodicyanobenzoquinone was added thereto, and the mixture was heated under reflux for 1.5 hours. After the mixture was left standing for cooling to room temperature, 500 ml toluene was added thereto, and the resulting precipitates were filtered off and washed with toluene several times. The filtrate was concentrated and the resulting crude product was purified by silica gel column chromatography to give 10.3 g of 5,8-dimethyl-2-naphthaldehyde as colorless crystals.