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

HRID 1940601Notes

Reaction equation

HRID 1940601 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-dioneYield 93.3%

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). Next 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 35.09 g of yellow-orange solid. The solid was recrystallized from isooctane to give 31.96 g, 85% of the dione, 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

Sources & evidence

ORD record
ord-0f6f5497164445f98f5a2bf7e8606de2
Source dataset
uspto-grants-1997_12
Patent number
US05700816

Reaction notes

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