Hydrochloric Acid → 4-Hexyloxy2,5-dicyanophenol

Participants

Reaction Conditions

Reaction Steps

In a 300 ml-reaction vessel, 350 g (2.19×10-1M) of 2,5-dicyanohydroquinone, 23.8 g (1.44×10-1M) of n-hexylbromide, 20.0 g (1.45×10-1M) of potassium carbonate and 180 ml of DMF were placed, followed by stirring for 3 hours at 120° C. After the reaction, the reaction mixture was cooled and poured into 500 ml of 4N-hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 17.6 g of a crude product. The crude product was dissolved in ethanol and treated with activated carbon, followed by recrystallization from ethanol to obtain 8.2 g of 4-hexyloxy2,5-dicyanophenol (Yield: 22.9%).

Provenance & Evidence