2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Formyl-6-phenylphenol

Participants

Reaction Steps

To a solution of 2-hydroxy-3-phenylbenzyl alcohol (2.00 g, 10 mmol) in dioxane (100 ml) was added 2,3- dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.50 g, 11 ml) at room temperature. The reaction mixture immediately became a black solution. This solution was stirred at room temperature for 2 hours and further heated under refluxing for 2 hours. The solvent was removed under reduced pressure to obtain deep-black oily residue. This was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.63 g (82%) of 3-phenylsalicylaldehyde as a light yellow oil.

Provenance & Evidence