1-(3-Methylbutoxy)-4-nitrobenzene → Aniline, p-(isopentyloxy)-

Participants

Reaction Steps

5% Palladium on charcoal (100 mg) was added in one portion to a stirred solution of 1-[(3-methylbutyl)oxy]4-nitrobenzene (intermediate 4, 2.00 g, 9.56 mmol) in ethyl acetate (40 mL) at room temperature under a nitrogen atmosphere. The nitrogen was replaced with hydrogen and stirring was continued for 4 h. The hydrogen was replaced with nitrogen then the crude reaction mixture was filtered through a plug of celite. The solute was evaporated to dryness to give the title compound as a colourless oil (1.71 g, 100%) which was used without purification. LC/MS: 2.29 min; z/e 180, calcd (M+1) 180. 1H NMR (400 MHz; CDCl3): 0.95 (6H), 1.65 (2H), 1.85 (1H), 3.10 (2H), 3.90 (2H), 6.65 (2H), 6.75 (2H).

Provenance & Evidence