Formaldehyde → Benzenemethanol, 2-hydroxy-3-methoxy-5-(2-propenyl)-

Participants

Reaction Steps

In a 2 liter round bottom flask equipped with nitrogen inlet and magnetic stirrer was dissolved eugenol, 99% (Alfa Aesar) in a solution comprised of 286 g NaOH in 1.2 L water at 0° C. A solution of formaldehyde (828 g, 10.2 mol), 37 wt. % solution in water, A.C.S. reagent (Sigma-Aldrich) was added dropwise to the stirring solution. The mixture was stirred under nitrogen at ambient temperature for 4 hours and then 55° C. for 20 h. The reaction mixture was poured into 1 L ethyl acetate and washed with 1 N HCl and deionized water. The crude product containing ˜30 mol % unreacted eugenol was used in the next step without further purification.

Provenance & Evidence