Sulfuric Acid → A 643C

Participants

Reaction Steps

A mixture (1:1.1) of 2-methylhept-1-ene and 2-methylhept-2-ene (4.0 g) was added to a suspension of aminoacetonitrile bisulphate (5.5 g; 1 mol equiv.) in acetic acid (22 ml). The resultant mixture was warmed to 40°. Conc. sulphuric acid (4.5 ml) was then added over 10 minutes with stirring, so that the temperature did not rise above 70°. The mixture was left for 1 hour and then poured into ice-water (200 g). The aqueous phase was washed with ether (2×100 ml), basified with 10 N sodium hydroxide solution (100 ml) (pH 14), and extracted with ether (3×100 ml). The combined ether extracts were washed with water (50 ml), dried, and evaporated in vacuo (Buchi; 20°) to give the product as a yellow oil, which was dried at 0.2 mm/0.5 h/r.t. By t.l.c., i.r. and n.m.r. this product was identical with 2-amino-N-(1,1-dimethylhexyl)acetamide prepared from 2-methylheptan-2-ol.

Provenance & Evidence