Furfuryl Alcohol → (5-((Diethylamino)methyl)furan-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-furfuryl alcohol (8.24 g; 84 mmol) in 55 ml of acetic acid was added dropwise a solution of N,N,N',N'-tetraethyl-methylenediamine (20 g; 126 mmol)in 25 ml of acetic acid, and the solution was stirred at 0° C. for 30 minutes and at room temperature for 17 hours. The above solution was concentrated in vacuo, the residue was basified with dropwise addition of 30% of NaOH solution at 0° C. (to pH=11), and the mixture was extracted with ethyl acetate. The mixture was filtered, the organic layer was dried over sodium sulfate and concentrated in vacuo to yield a brown oil. The oil was distilled with a Kugelrohr Apparatus to afford 12.33 g (80%) of 5-diethylaminomethyl-2-hydroxymethylfuran as a yellow oil, b.p. 140° C./1 mm.

Provenance & Evidence