[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14]O.[C:16]([O:19][C:20](=O)[CH3:21])(=[O:18])[CH3:17].[N+:23]([O-])([OH:25])=[O:24].C(O)(=[O:29])C>O>[C:16]([O:19][CH2:20][CH2:21][O:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH2:14][CH2:13][O:12][C:11](=[O:29])[CH3:10])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24])(=[O:18])[CH3:17]
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.
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