4-Nitrophenol → Nitrobenzene

Participants

Reaction Steps

A suspension of 5 g (36 mmol) of 4-nitrophenol in 250 ml of xylene was treated with a solution of 1.63 g (41 mmol) of sodium hydroxide in 20 ml of water and the mixture was stirred at room temperature for 30 minutes. The mixture was then treated with 7.5 g (54 mmol) of potassium carbonate and 5.11 g (36 mmol) of dimethylaminoethyl chloride hydrochloride. The mixture was heated at reflux for 2 hours and then for a further 24 hours with azeotropic removal of water. The mixture was filtered while hot and the solid was washed with hot xylene. The combined filtrate and washings were evaporated and the residue was distilled under a high vacuum to give 1.28 g (20%) of 4-[2-dimethylamino)ethoxy]nitrobenzene as an orange colored liquid.

Provenance & Evidence