3-(Dimethylamino)phenol → HCID 20312681, compound

Participants

Reaction Steps

A 407 g (7.68 moles) portion of acrylonitrile and 500 g (3.65 moles) of m-dimethylaminophenol were placed in a 3-l, 3-necked flask equipped with a stirrer and reflux condenser with a drying tube. The solution was treated with 4 g (0.17 mole) of metallic sodium, over 0.7 hr., with an observed temperature rise from 10° to 24°. The reaction mixture was heated to reflux over 0.8 hr., refluxed for 22 hrs., cooled, treated with 11 ml of glacial acetic acid and the excess acrylonitrile removed under reduced pressure. The residue was taken up in 3.8-l of ether, decanted from a purple resinous material, stored over Darco overnight and filtered. The filtrate was stripped of ether under reduced pressure to give 590 g (80%) of the desired nitrile (brown).

Provenance & Evidence