Vanillin → Veratraldehyde

Participants

Reaction Conditions

Reaction Steps

In a three-neck flask (capacity 100 ml) equipped with a mechanical stirrer and reflux condenser, 20 ml of dimethylformamide (anhydrous), 5.00 g (0.033 mol) of vanillin and 5.00 g (0.036 mol) of anhydrous potassium carbonate were placed and the mixture was heated under a nitrogen atmosphere to 100° C. The mixture was a clear to amber solution of vanillin with carbonate in suspension. To this mixture was added 5.00 ml (0.043 mol) of trimethyl phosphate over about 5 minutes while maintaining the reaction temperature below 125° C. The mixture was maintained at about 80° C. for one hour and then cooled to 40° C. The mixture was poured into 200 ml water and extracted two times with 50 ml of methylene chloride. The methylene chloride extracts were washed twice with 100 ml of water. The combined extracts were dried over anhydrous potassium carbonate, filtered, and concentrated to give 5.3 g (95%) of veratraldehyde as a pale oil.

Provenance & Evidence