Toluene → p-Vinylbenzyl chloride

Participants

Reaction Conditions

Reaction Steps

A flame dried 1-L round bottom flask was charged with AIBN (1.9 g, 11.6 mmol) and 50 mL of anhydrous toluene. To this stirred solution was added chloromethylstyrene (76.25 g, 500 mmol) in toluene (430 mL). Argon was bubbled through the mixture; it was then warmed to 78-80° C. with stirring for 22 hrs under a blanket of argon. Approximately 50 mL of hexane was added to the flask and the whole mixture was then poured into 750 ml of hexane. A taffy-like precipitate formed. The precipitate was collected and washed a couple of times with water. The precipitate was then dissolved in THF. The THF solution was filtered. Adding petroleum ether precipitated the product that was then separated from the mother liquor. The solid was dissolved again in THF, and finally precipitated in methanol. The product was collected and dried overnight at 50° C. in a vacuum oven. This gave the title compound as a brittle, white powder (36.16 g). GPC analysis that gave the following results:

Provenance & Evidence