Syringaldehyde → 3,4,5-Trimethoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

In a three-neck flask (capacity 100 ml) equipped with a mechanical stirrer and reflux condenser, 10.0 g (0.054 mol) of syringaldehyde 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. To this mixture was added 8.00 ml (0.094 mol) of dimethyl sulfite over about 5 minutes while maintaining the reaction temperature below 125° C. The pasty mixture was maintained at about 100° C. for three hours and then cooled to 25° C. and quenched with 50 ml water. The mixture was extracted with 100 ml of methylene chloride. The extracts were washed with water and concentrated in vacuo to give 4.2 g of 3, 4, 5-trimethoxybenzaldehyde.

Provenance & Evidence