Réaction #2028866

Équation de réaction

HCl

Ethyl trifluoroacetate

sodium methoxide

4′-chloroacetophenone

→

yellow-orange solid

Rendement 93.3%

4,4,4-trifluoro-1-[4-(chloro)phenyl]-butane-1,3-dione

Rendement 93.3%

Solvants

methyl tert-butyl ether

methyl tert-butyl ether

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded to the reaction dropwise over 5 minutes
2. 2
   workup.ADDITIONwas added
3. 3
   AutreThe organic layer was collected
4. 4
   Lavagewashed with brine (75 mL)
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

Ethyl trifluoroacetate (23.52 g, 166 mmol) was placed in a 500 mL three-necked round bottom flask, and dissolved in methyl tert-butyl ether (75 mL). To the stirred solution was added 25% sodium methoxide (40 mL, 177 mmol) via an addition funnel over a 2 minute period. Next 4′-chloroacetophenone (23.21 g, 150 mmol) was dissolved in methyl tert-butyl ether (20 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (15.75 hours), 3N HCl (70 mL) was added. The organic layer was collected, washed with brine (75 mL), dried over MgSO4, filtered, and concentrated in vacuo to give a 35.09 g of yellow-orange solid. The solid was recrystallized from iso-octane to give 31.96 g (85%) of the dione: mp66°-67° C.

Source