Hydrogen Peroxide → 1,3-Dichloro-2-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

1.32 g (4.0 mmol) of sodium tungstate dihydrate and 4.0 g (40 mmol) of concentrated sulfuric acid were added to a solution of 16.2 g (100 mmol) of 2,6-dichloroaniline in 120 ml of methanol, and the mixture was heated to 40° C. 30 ml (291 mmol) of a 30% hydrogen peroxide solution was added dropwise over 10 hours. The pH value at this time was 0.5. After the completion of the dropwise addition, the mixture was stirred at 40° C. for 9 hours. After the disappearance of the 2,6-dichloroaniline was confirmed by gas chromatography (area percentage method), a solution of 9.8 g (150 mmol) of 86% potassium hydroxide in 24.3 ml of methanol was added dropwise while the temperature of the reaction liquid was adjusted to 40° C. or less. After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, and the reaction was completed. After the completion of the reaction, 95 ml of toluene and 32 ml of water were added, and the mixture was stirred for a while, and filtered. The filtrate was separated. The obtained organic phase was washed with 8 ml of water, and then heated to reflux, and dehydrated. Thus, 2,6-dichloronitrobenzene was obtained as a toluene solution. This solution was analyzed by gas chromatography by the absolute calibration method, and as a result, the yield was 92%. The amount of the potassium hydroxide added is sufficient to make the pH condition alkaline.

Provenance & Evidence