Acetic Acid → HCID 19097122, compound

Participants

Reaction Steps

Hydroquinone-bis(2-hydroxyethylether (11.0 g; ) 0.057 mol) was stirred in glacial acetic acid (180 ml) and acetic anhydride (17.0 g; 0.166 mol) was added dropwise at room temperature. The mixture was heated to and maintained at reflux temperature for 18 hours, then cooled to below 20° C. and a mixture of 72% nitric acid (4.7 g; 0.054 mol) in glacial acetic acid (20 ml) was added dropwise over 20 minutes maintaining the temperature below 20° C. The reaction mixture was stirred below 20° C. for 16 hours then drowned into water and extracted with ether (2×150 ml). The combined organic extracts were washed with water, saturated sodium bicarbonate solution and brine. After drying and filtration the ether solution was evaporated to leave a brown oil which was dried over potassium hydroxide to give a yellow solid (12.83 g) which was recrystallised from water/ethanol (3:1) to give the title compound as a yellow solid (10.22 g) m.p. 67.5°-70° C.

Provenance & Evidence