Hydrochloric Acid → 1-(1,3-Benzodioxol-5-yl)-4,4-difluoro-1,3-butanedione

HRID 2084703Notes

Reaction equation

HRID 2084703 reaction equation
[F:1][CH:2]([F:8])[C:3](OCC)=[O:4].C[O-].[Na+].[CH2:12]1[O:20][C:19]2[CH:18]=[CH:17][C:16]([C:21](=[O:23])[CH3:22])=[CH:15][C:14]=2[O:13]1.Cl>CCOCC>[O:20]1[C:19]2[CH:18]=[CH:17][C:16]([C:21](=[O:23])[CH2:22][C:3](=[O:4])[CH:2]([F:8])[F:1])=[CH:15][C:14]=2[O:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 76622AcetopiperoneHCID 10942334Sodium Methoxide

Product 1

HCID 120809131-(1,3-Benzodioxol-5-yl)-4,4-difluoro-1,3-butanedione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl difluoroacetate (1.72 g, 11 mmol) was dissolved in ether (25 mL). To the stirred solution was added 25% sodium methoxide (2.38 g, 11 mmol) followed by 3′,4′-(methylenedioxy)acetophenone (1.64 g, 10 mmol). After stirring 16 hours, 1N HCl (25 mL) was added. The organic layer was collected and washed with water (2×25 mL), dried over magnesium sulfate, filtered, and concentrated. The resulting crude dione was used in the next step without further purification of characterization.

Workup

  1. customThe organic layer was collected
  2. washwashed with water (2×25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude dione was used in the next step without further purification of characterization

Sources & evidence

ORD record
ord-6a87eb3f1ef54249ba69d33298b08d10
Source dataset
uspto-grants-2004_04
Patent number
US06716991B1

Reaction notes

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