2,4,6-Trimethylaniline → HCID 18623783, compound

Participants

Reaction Steps

A solution of acetol (1′) (20 mL, 0.26 mol), 2,4,6-trimethylaniline (2′) (36.5 mL, 0.260 mol), and 4-toluenesulfonic acid monohydrate (0.21 g) were refluxed in benzene (115 mL) using a Dean-Stark trap to remove water. After 2 hours, ethyl cyanoacetate (27.7 mL, 0.26 mol) was added and heating was continued for 14 hours. The mixture was cooled to room temperature, concentrated, and the residue chromatographed (elution with 15% ethyl acetate in hexanes) to afford 21.4 g (29%) of compound (3′) as a yellow oil.

Provenance & Evidence