M-Xylene → HCID 12195664, compound

Temperature

0 °C

m-Xylene (34.1 g, 0.32 moles) and 2-bromoisobutyryl bromide (73.9 g, 0.32 moles) were stirred in methylene chloride (500 mL) at 0° C. as AlCl3 (108.98 g, 0.82 moles) was added slowly as a solid under a nitrogen flow over a 20 minute period of time. The reaction was then allowed to stir at 0° C. for 1 hour and then for 16 hours at 20° C. After the reaction period the mixture was poured on crushed ice and then filtered through diatomaceous earth (Celite™ brand). The mixture was then extracted with 1 M HCl (2×100 mL), 1 M NaHCO3 (1×100 mL), and H2O (1×100 mL) and the organic layer dried over MgSO4. Filtration followed by removal of the volatiles resulted in the isolation of a yellow oil. Vacuum distillation resulted in the isolation of the desired product as a pale yellow oil (50.4 g, 89.9 percent yield).

1. additionwas added slowly as a solid under a nitrogen flow over a 20 minute period of time
2. waitfor 16 hours at 20° C
3. customAfter the reaction period the mixture
4. additionwas poured
5. customon crushed ice
6. filtrationfiltered through diatomaceous earth (Celite™ brand)
7. extractionThe mixture was then extracted with 1 M HCl (2×100 mL), 1 M NaHCO3 (1×100 mL), and H2O (1×100 mL)
8. dry with materialthe organic layer dried over MgSO4
9. filtrationFiltration
10. customfollowed by removal of the volatiles
11. customresulted in the isolation of a yellow oil
12. distillationVacuum distillation

ORD record

ord-f5ff9833a1ab4bb8af10713fad4caf28

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06015868