Aniline → 2-sec-Butyl-6-iospropylphenol

Participants

Reaction Conditions

Reaction Steps

(−)-2-Sec-butyl-6-isopropylaniline (3) (1.92 g, 10 mmol) was dissolved in 20 ml 15% H2SO4 at 60° C., and then cooled to 0° C. A solution of NaNO2 (0.76 g, 11 mmol) in 8 ml water was added to the reaction mixture rapidly (˜30 sec) with vigorous stirring keeping temperature below 0° C. The solution was stirred for an additional 2 minutes, and then added in one portion to the suspension of Cu2O (1.5 g), in aqueous CuSO4×5H2O (10 g in 220 ml) with vigorous stirring at 50° C. Reaction mixture was stirred 30 min. and cooled to room temperature. The reaction was repeated five times with the same scale (total 9.13 g of aniline was used), and all reaction mixtures were combined. Organic material was extracted twice with ether (400 ml). The solvent was evaporated, and the compound purified by silica gel chromatography. CombiFlash chromatography (Hexane/EtAc) was performed and final product distilled (105-110*C/˜3 mm) (4.1 g (45%). Optical rotation: α20D=−7.58° (c=5, pentane). 1H NMR (250 MHz, chloroform-d1) δ 0.84-0.90 (t. 3H), δ 1.21-1.26 (m. 11H), δ 2.85-2.89 (m. 1H), δ 3.11-3.16 (m. 1H), δ 4.74 (s, 1H), δ 6.87-6.90 (t, 1H) δ 6.987-7.05 (m 2H).

Provenance & Evidence