[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].[OH-].[Na+].C=O.[C:17](OCC)(=[O:19])C>O>[CH2:7]([C:6]1[CH:10]=[C:1]([O:11][CH3:12])[C:2]([OH:3])=[C:4]([CH2:17][OH:19])[CH:5]=1)[CH:8]=[CH2:9]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.
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