C(Cl)(=O)C(Cl)=O.C(Cl)Cl.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:16][OH:17])([O-:12])=[O:11].C(N(CC)CC)C>C1COCC1.O>[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH:16]=[O:17])([O-:12])=[O:11]
To a solution of oxalylchloride (26 ml, 0.30 mol) in CH2Cl2 (600 ml) DMSO (43 ml, 0.60 mol) was added, maintaining the temperature between −50° C. and −65° C. To the reaction solution was then added 3,5-dinitrobenzyl alcohol (50g), in THF (100 ml), maintaining the temperature between −50° C. and −65° C. The reaction mixture was stirred at −65° C. for 30 minutes and then triethylamine (170 ml) was added at −50° C. and −65° C. The reaction temperature was then adjusted to room temperature and H2O (800 ml) was added. The organic phase was washed with sat. NaHCO3 (500 ml), 5 times with diluted HCl (300 ml) and finally brine. The organic phase was then dried over MgSO4 and the volatile solvents were removed at reduced pressure. The crude product was then triturated with heptane, which gave 45.8 g (89%) of 3,5-dinitrobenzaldehyde.
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