Vanillin → 4-[3-(4-Formyl-2-methoxyphenoxy)-2-hydroxypropoxy]-3-methoxybenzaldehyde

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Reaction Steps

Vanillin (91.2 g, 0.60 mol) is dissolved in water (500 mL) containing sodium hydroxide (24.0 g). To this solution is added 1,3-dichloro-2-propanol (38.7 g, 0.30 mol) and the reaction mixture is stirred and heated at reflux for 8 hours. Upon cooling to room temperature the product crystallizes and is collected by filtration, washed with water and dried. The crude product is recrystallized from 2 L ethanol, filtered, washed with ethanol and air dried. The purified product, 4,4'-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[3-methoxybenzaldehyde], is obtained as a white solid in a yield of 74.3 g; 68.7% of theory. Mass spectroscopy analysis supports the structure: ##STR23## A mixture of 4,4'-[(2-hydroxy-1,3-propanediyl)bis[3-methoxy-benzaldehyde] (3.60 g, 0.01 m), ethyl cyanoacetate (2.26 g, 0.02 m), ethanol (100 mL), piperidine (10 drops), and acetic acid (5 drops) is heated at reflux for 4 hours and then allowed to cool. The essentially white product is collected by filtration, washed with ethanol, and dried in air (yield--3.5 g). Mass spectrum analysis supports the following structure: ##STR24## The product, diethyl 3,3'-[(2-hydroxy-1,3-propanediyl)bis(oxy)bis(3-methoxy-4,1-phenylene)]bis[2-cyano-2-propenoate], has an absorption maximum (λmax) at 360 nm in methylene chloride.

Provenance & Evidence