Methanol → 2-(4-Tert-butylphenyl)ethan-1-amine

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Reaction Steps

14.8 g (0.10 mol), of p-tert-butyltoluene was dissolved in carbon tetrachloride, and 17.8 g (0.10 mol), of N-bromosuccinimide and 200 mg of benzoyl peroxide are added to the solution, and the mixture was refluxed for 2 hours. After cooling, insoluble matter was filtered off. The residue was washed with carbon tetrachloride and the filtrate was concentrated under reduced pressure. The residue was dissolved in n-hexane and the solution was dried with magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain 22.7 g (yield: 100%, however, the results of 1H-NMR revealed that the product was a mixture of the target compound:raw material:dibromo form=10:1:1), of p-tert-butylbenzylbromide. 10.6 g (0.10 mol), of sodium carbonate was added to 200 ml of a 40% methylamine-methanol solution, and 20 ml of the methanol containing 22.7 g (0.10 mol), of p-tert-butylbenzyl bromide was dropped in an ice bath. After taking out of the ice bath, the solution was stirred at room temperature for 41 hours. The methanol was distilled off under reduced pressure and water was added to the residue, followed by extraction with 400 ml of ether. The ether part was extracted twice with 200 ml and 100 ml, respectively, of 1N hydrochloric acid and the water part was extracted with ethyl acetate. Then, the water extract was changed to alkaline with an aqueous 2N sodium hydroxide solution and extracted with 400 ml of ether. After drying the extracts with magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=200:1→100:1→20:1), to obtain the target substance of 9.51 g (yield: 53.7%).

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