Vanillin → HCID 54028713, compound

Participants

Reaction Steps

Vanillin (30.4 g, 0.20 m) is dissolved in water (150 mL), containing sodium hydroxide (8.5 g). 1,4-Dibromo-2-butene (21.4 g, 0.1 m) is added and the reaction mixture heated at reflux for 6 hours. After the reaction mixture is cooled, the product is collected by filtration, washed with water, dried in air, and finally recrystallized from toluene (200 mL). The yield is 18.8 g (52.8% of the theoretical yield) of 4,4'-[2-butene-1,4-diylbis(oxy)]bis[3-methoxybenzaldehyde] as indicated by mass spectroscopy analysis. A mixture of 4,4'-[2-butene-1,4-diylbis(oxy)]bis[3-methoxybenzaldehyde] (3.56 g, 0.01 m), ethyl cyanoacetate (2.26 g, 0.02 m), ethanol (90 mL), and piperidine (10 drops) is heated at reflux for 4 hours. The reaction mixture is cooled and the product is collected by filtration, washed with ethanol, and dried in air (yield--4.3 g). Mass spectrum analysis supports the following structure: ##STR30## In methylene chloride, the product has an absorption maximum at 316 nm.

Provenance & Evidence