2-(Chloromethyl)-1-ethyl-4-nitrobenzene → HCID 20563889, compound

Participants

Reaction Steps

A mixture of α-chloro-2-ethyl-5-nitrotoluene (5.0 g; 0.025 mol), diethyl ketone (30 ml) and 5% platinum on carbon catalyst (Pt/C; 0.50 g) is charged to a pressure vessel. Next, the vessel is sealed, evacuated and purged with nitrogen and is then pressurized with hydrogen gas to 40 to 60 psig. The reaction mixture is agitated until the theoretical amount of hydrogen is taken up (2.5 hours). The vessel is then vented, the reaction mixture diluted with methylene chloride and filtered. The filtrate is concentrated under vacuum to yield an off-white solid (6.1 g). This solid is dissolved in 0.5 N hydrochloric acid (200 ml) at 90° C. The aqueous solution is then cooled to room temperature, extracted with ether (3x) and made alkaline. An oil separates and is removed by extraction with ether. The ether phase is washed with water, dried and concentrated under vacuum to afford 3.82 g (74.5%) of crude product, a brown oil, found to be 73.7% pure by glc.

Provenance & Evidence