Hydrochloric Acid → 4-(Hexadecyloxy)phenol

Participants

Reaction Conditions

Reaction Steps

To a 0° C. suspension, under argon, of 29 g of 60% sodium hydride in 350 ml of dimethylformamide is added dropwise over 40 minutes, 60.0 g of hydroquinone in 450 ml of dimethylformamide. The suspension is stirred at 0° C. for 1/2 hour; followed by the dropwise addition of 192 g of 1-iodohexadecane in 450 ml tetrahydrofuran. The reaction temperature is maintained at 0° C. during the addition of the alkyl halide; followed by stirring at room temperature for 3 hours. The mixture is poured carefully into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and concentrated in vacuo.

Provenance & Evidence