Hydrochloric Acid → 1,3-Butanedione, 4,4,4-trifluoro-1-[4-(methylthio)phenyl]-

HRID 1836980Notes

Reaction equation

HRID 1836980 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].CO.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=1)=[O:17].Cl>CC(OC)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=1)=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 745011-(4-(Methylthio)phenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 107301701,3-Butanedione, 4,4,4-trifluoro-1-[4-(methylthio)phenyl]-Yield 71%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

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%).

Workup

  1. customthe organic phase separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customto give an orange solid
  5. customThe orange solid was recrystallised from hot isopropanol

Sources & evidence

ORD record
ord-7b98414f270d4ad4b839366712d1cae1
Source dataset
uspto-grants-2004_08
Patent number
US06780870B2

Reaction notes

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