Reaction #2028866

Reaction equation

HCl

Ethyl trifluoroacetate

sodium methoxide

4′-chloroacetophenone

→

yellow-orange solid

Yield 93.3%

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

Yield 93.3%

Solvents

methyl tert-butyl ether

methyl tert-butyl ether

Conditions

Workup

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

Procedure

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