Veratraldehyde → 3,4-Dimethoxytoluene

Participants

Reaction Steps

A mixture of veratraldehyde (91.5g), KOH (100 g), 95% hydrazine (75 ml) and ethylene glycol (700 ml) was heated at reflux until the KOH disappeared (30 min). The hydrazone then separated as a yellow solid and mild foaming occurred. The heating was continued at reflux causing evolution of N2 and vigorous frothing. After 3 hr., the solution was cooled, poured into 1.5 l of cold water and the resulting oil was extracted into ether. The combined extracts were washed with water, dried and evaporated to yield a yellow oil which was distilled to give 65.7 g of the product, 3,4-dimethoxy toluene as a colorless oil (bp 68°-72°at 0.05 mm).

Provenance & Evidence