Dimethylamine → HCID 11458025, compound

Participants

Reaction Steps

To a 25 mL round bottom flask equipped with a mechanical stirrer and a thermometer was added 4 mL (%Wt/Vol. Phenol to Solvent--50%) of isopropanol, followed by 2.0 grams (0.0164 mole--1.0 equiv.) of m-ethylphenol and then 2.22 grams (0.0197 mole--1.2 equiv.) of an aqueous 40% N,N-dimethylamine solution. The mixture was stirred at ambient temperature to effect dissolution, and 0.59 gram (0.0197 mole--1.2 equiv.) of paraformaldehyde was added. The reaction mixture began to exotherm so it was cooled to ambient temperature where it stirred for 17 hours. After this time, the reaction mixture was concentrated under reduced pressure to a residue, and the residue was taken up in heptane and water. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 2.8 grams of 2-[(N,N-dimethylamino)methyl]-5-ethylphenol (88.7% yield). Gas Chromatography (GC) analysis of the product indicated the presence of about 7% of an impurity. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence