Dehydroacetic acid → Methyl 3,5-dioxohexanoate

HRID 628816Notes

Reaction equation

HRID 628816 reaction equation
C[O-:2].[Mg+2].C[O-].C[C:7]1[O:14][C:12](=O)[CH:11]([C:15]([CH3:17])=[O:16])[C:9](=[O:10])[CH:8]=1>CO>[O:10]=[C:9]([CH2:11][C:15](=[O:16])[CH3:17])[CH2:8][C:7]([O:14][CH3:12])=[O:2]

Participants

4

Reactant 2

HCID 122903Dehydroacetic acidHCID 164537Methanol, magnesium salt (2:1)

Product 1

HCID 538296Methyl 3,5-dioxohexanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Magnesium methoxide (6% in MeOH, 530 mL) was added to a suspension of dehydroacetic acid (31 g) in methanol (600 mL) at room temperature. The reaction mixture was refluxed and stirred for 5 h. The solvent was removed and the residue dissolved in HCl 1M (1.5 L). The aqueous phase was extracted with EtOAc (2×750 mL) and then the solvent was evaporated under reduced pressure to give a yellow oil, which was filtered on a silica cartridge using dichloromethane as eluent. After the solvent removal, methyl 3,5-dioxohexanoate was obtained as a light yellow oil (19.9 g).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in HCl 1M (1.5 L)
  4. extractionThe aqueous phase was extracted with EtOAc (2×750 mL)
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a yellow oil, which
  7. filtrationwas filtered on a silica cartridge
  8. customAfter the solvent removal

Sources & evidence

ORD record
ord-71e3c0fe882344ec8ebc2c59bc5460c9
Source dataset
uspto-grants-2016_04
Patent number
US09315470B2

Reaction notes

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