Dichloromethane → 3,5-dinitrobenzaldehyde

HRID 1280184Notes

Reaction equation

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]

Participants

Conditions

Temperature: -65 °C

Procedure

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.

Workup

temperaturemaintaining the temperature between −50° C. and −65° C
customwas then adjusted to room temperature
washThe organic phase was washed with sat. NaHCO3 (500 ml), 5 times with diluted HCl (300 ml) and finally brine
dry with materialThe organic phase was then dried over MgSO4
customthe volatile solvents were removed at reduced pressure
customThe crude product was then triturated with heptane, which

Sources & evidence

ORD record: ord-559a51bd6d514a9ea7d285f4b0c5ae81
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448442B1

Reaction notes

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