Hydrochloric Acid → methyl 6,6,6-trifluoro-3,5-dioxohexanoate

HRID 1394462Notes

Reaction equation

HRID 1394462 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[O:6]C(=O)[CH:4]=1.[CH3:14][O-:15].[Mg+2].[CH3:17][O-:18].Cl>>[F:10][C:9]([F:12])([F:11])[C:7](=[O:6])[CH2:8][C:3](=[O:2])[CH2:4][C:14]([O:18][CH3:17])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 164537Methanol, magnesium salt (2:1)HCID 68743481HCID 68743481, compound

Product 1

HCID 10192666methyl 6,6,6-trifluoro-3,5-dioxohexanoateYield 26%

Procedure

A solution of 4-methoxy-6-trifluoromethylpyran-2-one (10 g, 52 mmol) in a methanolic magnesium methanolate solution (8.5% Mg(OMe)2, 62.8 g, 61 mmol) was heated under reflux for 2 hours. Concentrated aqueous HCl (25.5 g, 250 mmol) was added to the reaction solution, and the mixture was heated under reflux for a further 2 hours, then cooled and concentrated in vacuo to about 20% of the initial volume. The residue was mixed with 10 mL each of methylene chloride and water. The organic phase was separated off, washed with water, dried over sodium sulfate and concentrated. Kugelrohr distillation at 0.04 mbar and about 160° C. afforded methyl 6,6,6-trifluoro-3,5-dioxohexanoate (2.8 g, 13 mmol, 26%) as a pale yellow oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for a further 2 hours
  4. temperaturecooled
  5. concentrationconcentrated in vacuo to about 20% of the initial volume
  6. additionThe residue was mixed with 10 mL each of methylene chloride and water
  7. customThe organic phase was separated off
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. distillationKugelrohr distillation at 0.04 mbar and about 160° C.

Sources & evidence

ORD record
ord-a5dd844265a14f019d75efd1100806cb
Source dataset
uspto-grants-2008_03
Patent number
US07348450B2

Reaction notes

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