Reaktion #937313

Reaktionsgleichung

m-Xylene

2-bromoisobutyryl bromide

AlCl3

→

desired product

Ausbeute 90.4%

2,4,6-Trimethylindanone

Ausbeute 90.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added slowly as a solid under a nitrogen flow over a 20 minute period of time
2. 2
   workup.WAITfor 16 hours at 20° C
3. 3
   SonstigeAfter the reaction period the mixture
4. 4
   workup.ADDITIONwas poured
5. 5
   Sonstigeon crushed ice
6. 6
   Filtrationfiltered through diatomaceous earth (Celite™ brand)
7. 7
   ExtraktionThe mixture was then extracted with 1 M HCl (2×100 mL), 1 M NaHCO3 (1×100 mL), and H2O (1×100 mL)
8. 8
   Trocknenthe organic layer dried over MgSO4
9. 9
   FiltrationFiltration
10. 10
    Sonstigefollowed by removal of the volatiles
11. 11
    Sonstigeresulted in the isolation of a yellow oil
12. 12
    workup.DISTILLATIONVacuum distillation

Vorschrift

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).

Quelle