1,2-Dichlorobenzene → 2-(6-Hydroxy-2-naphthyl)-5-butylbenzooxazole

Participants

Reaction Conditions

Reaction Steps

5.40 g (14.3 m mole) of 2-(6-acetoxy-2-naphthoylamino)-4-butylphenol, 0.43 g of p-toluenesulfuric acid monohydrate and 40 ml of O-dichlorobenzene were placed in a 100 ml round-bottom flask, followed by heating and stirring for 30 minutes at 200-203° C. After the reaction, O-dichlorobenzene was distilled off under reduced pressure. To the resultant, 2.00 g (30.3 m mole) of potassium hydroxide and 60 ml of ethanol were added, followed by heating and stirring for 20 minutes at 60° C. After the reaction, the reaction mixture was poured into 600 ml of water. To the reaction mixture, 8 ml of chloric acid was added to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from a mixture solvent of acetoneethanol to obtain 2.18 g of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole (Yield: 42.4%).

Provenance & Evidence