Hydrochloric Acid → 1-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dione

HRID 2187017Notes

Reaction equation

HRID 2187017 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>C(OC)(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium Methoxide

Product 1

HCID 27738321-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dione

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Ethyl trifluoroacetate (23.52 g, 166 mmol) was dissolved in methyl tert-butyl ether (75 mL). To the stirred solution was added 25 weight % sodium methoxide (40 mL, 177 mmol). 4′-Chloroacetophenone (23.21 g, 150 mmol) was dissolved in methyl tert-butyl ether (20 mL) and added to the reaction dropwise. 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 yellow-orange solid. The solid was recrystallized from isooctane to give the dione (31.96 g, 85%): mp 66-67° C.

Workup

  1. additionadded to the reaction dropwise
  2. additionwas added
  3. customThe organic layer was collected
  4. washwashed with brine (75 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow-orange solid
  9. customThe solid was recrystallized from isooctane
  10. customto give the dione (31.96 g, 85%)

Sources & evidence

ORD record
ord-195065cdd64c48269a63c2d588dda7eb
Source dataset
uspto-grants-2002_06
Patent number
US06407140B1

Reaction notes

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