Hydrochloric Acid → Benzylvinylether

Participants

Reaction Steps

45 g (0.25 equivalent) of a dicyclopentadiene skeleton phenolic resin (DPP-3H, special phenolic resin, available from Nippon Petrochemical Co., Ltd.), 38.1 g of vinylbenzyl chloride (CMS-AM; purity of 91%; 0.25 mol; m-/p-isomers: 50/50 wt % mixture; available from Seimi Chemical Co., Ltd.), 2.4 g of tetra-n-butylammonium bromide, 0.038 g of 2,4-dinitrophenol, and 200 g of methyl ethyl ketone were charged into a 1-liter four-necked flask equipped with a thermoregulator, a stirrer, a cooling condenser, and a dropping funnel and dissolved under stirring. 40 g of a 50 wt % aqueous solution of NaOH (NaOH purity of 95%, 0.475 mol) was added dropwise at 75° C. to the obtained solution over 20 minutes, and the whole was stirred at 75° C. for additional 4 hours. After the obtained reaction mixture was cooled to room temperature, the mixture was neutralized with 2N hydrochloric acid, and 100 g of toluene was added. An organic layer was then washed with 300 g of distilled water three times. After methyl ethyl ketone was removed under reduced pressure, a reaction product was precipitated in 300 ml of methanol to collect a solid matter through filtration, which was then dried at 50° C. in a vacuum oven to obtain a vinylbenzyl ether compound at an yield of 95%. The obtained compound is designated as Compound 19.

Provenance & Evidence