2-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzene → 3-(Tert-butoxy)-2-methylaniline

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Reaction Steps

To a solution of 2-methyl-3-tert-butoxynitrobenzene K3 (1.31 g; 6.26 mmol) in absolute ethanol (30 mL) was added 10% Pd/C catalyst (130 mg). The solution was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 63 h. The reaction mixture was filtered through a Celite pad, rinsed with absolute EtOH and evaporated to dryness to provide 2-methyl-3-tert-butoxyaniline K4 (1.1 g; 6.14 mmol; 98% yield). M.S. 180 (M+H)+. Homogeneity by HPLC (TFA) @ 220 nm: 96%

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