Toluene → p-Vinylbenzyl chloride

Temperature

79 °C

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:

1. dry with materialA flame dried 1-L round bottom flask
2. customArgon was bubbled through the mixture
3. additionApproximately 50 mL of hexane was added to the flask
4. additionthe whole mixture was then poured into 750 ml of hexane
5. customA taffy-like precipitate formed
6. customThe precipitate was collected
7. washwashed a couple of times with water
8. dissolutionThe precipitate was then dissolved in THF
9. filtrationThe THF solution was filtered
10. customAdding petroleum ether precipitated the product that
11. customwas then separated from the mother liquor
12. dissolutionThe solid was dissolved again in THF
13. customfinally precipitated in methanol
14. customThe product was collected
15. customdried overnight at 50° C. in a vacuum oven

ORD record

ord-edb41161b27c42fd8de27ce04714e9cb

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07981408B2