trans- (CAS NO.: ), which is also known as (E)-stilbene, could be produced through the following synthetic routes.

In a 4-l. beaker, equipped with a powerful mechanical stirrer which reaches nearly to the bottom, are placed 500 ml. of water and 50 g. of mercuric chloride. The stirrer is started, and 200 g. (3.06 gram atoms) of zinc dust is rapidly sifted into the suspension. Stirring is continued until the mercuric chloride dissolves (about 20–30 minutes). The zinc is then allowed to settle, the supernatant liquid is removed by decantation, and the amalgam is filtered and washed with 200 ml. of water. The zinc amalgam is returned to the beaker, which is now surrounded by an ice bath, and 500 ml. of 95% ethanol and 100 g. (0.48 mole) of benzoin are added. The stirrer is started, and 500 ml. of concentrated hydrochloric acid is added through a dropping funnel at such a rate that addition is complete in about 2 hours; throughout the reaction the temperature is maintained below 15°. Stirring is continued for about 2 hours more.

About 2 l. of cold water is added to the reaction mixture, and the insoluble material is collected on a Büchner funnel. The precipitate is transferred to a 2-l. beaker and extracted with two 600-ml. portions of hot ethanol. The combined extracts, on cooling, deposit long needles of stilbene which weigh 55–59 g. and melt at 116–121°. These are filtered with suction and are recrystallized from 600 ml. of 95% ethanol. The yield is 45–48 g. (53–57%) of colorless needless melting at 123–124°.