(CAS NO.: ), which is also known as veratric aldehyde, could be produced through the following synthetic route.

In a 3-l. three-necked flask a mixture of 182 g. (1.2 moles) of vanillin and 450 cc. of boiling water is ed on a steam bath. A solution of sodium hydroxide is prepared by dissolving 150 g. of u.s.p. sodium hydroxide in 200–300 cc. of water and diluting to 750 cc. A 360-cc. portion of this solution is heated to about 100° and added in one lot to the hot mixture of vanillin and water. The flask is now fitted with a reflux condenser, mechanical stirrer, and 250-cc. separatory funnel.

Heating is continued on a steam bath, and 189 g. (142 cc.) of methyl sulfate is added through the separatory funnel just rapidly enough to maintain the gentle ebullition which starts after the addition of the first 10–15 cc. After the addition of all the methyl sulfate, which requires about one hour, the reaction mixture is heated for forty-five minutes longer and an additional portion of 39 g. (30 cc.) of methyl sulfate is added at the same rate as the first portion. At the end of this addition the reaction mixture should show an acid reaction to litmus. After ten minutes' heating the reaction mixture is rendered slightly alkaline by the addition of about 60 cc. of the sodium hydroxide solution (prepared above), and another 39-g. portion of methyl sulfate is added. The alternate addition of sodium hydroxide solution and of methyl sulfate (39-g. portions) is repeated twice more, so that a total of 345 g. (2.7 moles) of methyl sulfate is added. The reaction mixture is then made strongly alkaline by the addition of 150 cc. of the sodium hydroxide solution and is heated for twenty minutes after the last addition of methyl sulfate. The reaction mixture is cooled rapidly to 25°with continued stirring, and the veratraldehyde is extracted with three 300-cc. portions of ether.

The combined ether extracts are dried over anhydrous magnesium sulfate, and the ether is distilled. There remains a slightly yellow oil which soon solidifies. The yield is 164–173 g. (82–87 per cent of the theoretical amount) of veratraldehyde melting at 43–44.5°. This product is sufficiently pure for many purposes, but it can be purified further with slight loss by distillation under diminished pressure. From 164 g. of the above product there is obtained 156 g. of pure veratraldehyde, boiling at 153°/8 mm. and melting at 46°. Since this aldehyde is easily oxidized in the air it should be stored in a tightly corked or sealed container.