Reaction #6789

Reaction equation

4-Methylthioacetophenone

ethyl trifluoroacetate

sodium methoxide

methanol

Hydrochloric acid

→

title compound

Yield 71.0%

4,4,4-Trifluoro-1-[4-(methylthio)phenyl]butane-1,3-dione

Yield 71.0%

Solvents

MTBE

Conditions

Workup

1. 1
   Otherthe organic phase separated
2. 2
   Washwashed with brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Otherto give an orange solid
5. 5
   OtherThe orange solid was recrystallised from hot isopropanol

Procedure

To a solution of ethyl trifluoroacetate (7.95 ml, 1.1 eq) in MTBE (125 ml) was added dropwise 25% sodium methoxide in methanol (16 ml, 1.2 eq). 4-Methylthioacetophenone (Aldrich, 10 g, 0.06 mol) was added portionwise and the mixture stirred at ambient temperature overnight. 2N Hydrochloric acid (40 ml) was added cautiously and the organic phase separated, washed with brine and dried (Na2SO4) to give an orange solid. The orange solid was recrystallised from hot isopropanol to give the title compound as a yellow crystalline solid (11.25 g, 71%).

Source