Benzene → HCID 21432285, compound

Participants

Reaction Steps

Trimethylhydroquinone (7.61 g.) was suspended under N2 in 60 ml. of benzene and 15 ml. of 25% dimethylamine in H2O. Aqueous formaldehyde solution (37%, 7.5 ml.) was added over 15 minutes and stirring was continued at 25° overnight. The benzene layer was washed with H2O, dried over Na2SO4, and stripped of solvent to give 2-dimethylaminomethyl-3,5,6-trimethylhydroquinone as a light tan solid. A similarly prepared sample of this material, which is quite susceptible to air oxidation, had a m.p. of 103°-108.5° with decomposition, after isolation from methanol-H2O.

Provenance & Evidence