Sulfuric Acid → 5-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one

HRID 1648185Notes

Reaction equation

HRID 1648185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:12]([CH3:14])=[O:13])[C:9]([OH:11])=[O:10].C(O[C:19](=O)[CH3:20])(=O)C.S(=O)(=O)(O)O.[C:27](=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:11])[O:10][C:19]([CH3:20])([CH3:27])[O:13][C:12]=1[CH3:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 3023024Acetyl(2-fluorophenyl)acetic acid

Product 1

HCID 153008465-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2-fluorophenyl)acetoacetic acid (5.1 g), acetone (4.2 ml), and acetic anhydride (5.4 ml) was kept at -20° C. and concentrated sulfuric acid (0.3 ml) was added thereto. This was kept at -15° C. and the reaction was carried out for 48 hours. The reaction mixture was added to an aqueous 10 % sodium carbonate solution (150 ml) which was ice-cooled, and the mixture was stirred for a short time at room temperature. White crystals which formed were collected by filtration, and washed well with water and then with hexane. The crystals obtained were dried well under reduced pressure to obtain the captioned compound (5.2 g).

Workup

  1. customwas kept at -20° C.
  2. customThis was kept at -15° C.
  3. temperaturecooled
  4. customWhite crystals which formed
  5. filtrationwere collected by filtration
  6. washwashed well with water
  7. customThe crystals obtained
  8. customwere dried well under reduced pressure

Sources & evidence

ORD record
ord-bdc3e776827c407685d5ec95f971d9c4
Source dataset
uspto-grants-1995_07
Patent number
US05436224

Reaction notes

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