Diphenylmethyl vinyl ether (CAS no.: ), which is also known as , 1,1'-[(ethenyloxy)methylene]bis-, could be produced through the following synthesis routes.

A 250-ml., three-necked, round-bottomed flask equipped with a sealed mechanical stirrer, a dropping funnel, and a reflux condenser is charged with 13.3 g. (0.0522 mole) of 2-(diphenylmethoxy)-N,N-dimethylethylamine and 50 ml. of acetone. The solution is stirred, and 8.1 g. (0.057 mole) of in 15 ml. of acetone is added dropwise over 5 minutes. After the addition is complete, the mixture is stirred for 30 minutes, then cooled to 0–10° with an ice bath. The crystalline product is filtered and washed with 15 ml. of acetone and 30 ml. of diethyl ether, yielding 20.0–20.2 g. (97–98%) of colorless, crystalline methiodide, m.p. 194–196°.

An excess (60 g., ca. 0.26 equivalent) of anion exchange resin (OH- form) in a 500-ml. Erlenmeyer flask is stirred with 200 ml. of methanol for 5 minutes. The methanolic slurry of resin is transferred to a 6.5 cm. × 25 cm. chromatography column, using 50–100 ml. of methanol to aid in the transfer. The resin column is washed with 750 ml. of methanol, added gradually so as to maintain about a 1–2.5 cm. solvent head above the upper resin level. About two-thirds of the resin slurry is poured from the column (using about 100 ml. of methanol to aid the transfer) into a suspension of 19.9 g. (0.0499 mole) of the methiodide in 50 ml. of methanol. The mixture is stirred and heated gently on a water bath, dissolving the crystalline methiodide. The resulting resin suspension is poured onto the column containing the remaining one-third of the resin. Additional methanol (ca. 50 ml.) is required to facilitate transferral. The column is eluted with about 500 ml. of methanol until the eluent no longer affords an alkaline reaction to pH paper. The methanolic eluent is concentrated under reduced pressure (10–25 mm.), and the residual liquid is gradually heated to 100° under the water-aspirator vacuum. Following completion of thermal decomposition, as evidenced by the end of gas evolution (ca. 5–10 minutes), the residue is dissolved in 250 ml. of ether. The ether solution is washed with 100 ml. of 0.2 N sulfuric acid and 100 ml. of water, dried over anhydrous magnesium sulfate, and filtered. The filtrate is concentrated, and distillation of the residue gives 8.5–9.0 g. (81–86%) of diphenylmethyl vinyl ether as a colorless liquid, b.p. 163–167° (18 mm.), n_D²⁵ 1.5716.

Notice: Methyl iodide, in high concentrations for short periods or in low concentrations for long periods, can cause serious toxic effects in the central nervous system. Accordingly, the American Conference of Governmental Industrial Hygienists2 has set 5 p.p.m., a level which cannot be detected by smell, as the highest average concentration in air to which workers should be exposed for long periods. The preparation and use of methyl iodide should always be performed in a well-ventilated fume hood. Since the liquid can be absorbed through the skin, care should be taken to prevent contact.