Synthesis
5-(tert-butyl)-1,3-dimethyl-2-nitrobenzene (15 g, 0.072 mol) was mixed with stannous chloride (41 g, 0.216 mol) in 300 mL of ethanol and the reaction was heated at reflux for 24 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and neutralized by slowly adding aqueous potassium hydroxide solution under stirring. Subsequently, the reaction mixture was extracted with ethyl acetate to separate the organic phase. The organic phase was purified by column chromatography to give 7 g of 4-tert-butyl-2,6-dimethyl-aniline ([Intermediate 8-b]) in 58% yield.
References
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1 - 8
[2] Chemistry Letters, 1983, p. 1373 - 1374
[3] Journal of Chemical Research - Part S, 2000, # 6, p. 290 - 291
[4] Patent: KR2015/124677, 2015, A. Location in patent: Paragraph 0291; 0296-0299
[5] Organometallics, 2010, vol. 29, # 24, p. 6723 - 6731
