Sulfuric Acid → 5-Methylcyclohexane-1,3-dione

HRID 595083Notes

Reaction equation

HRID 595083 reaction equation
COC([C:5]1[CH:10]([CH3:11])[CH2:9][C:8](=[O:12])[CH2:7][C:6]=1[OH:13])=O.OS(O)(=O)=O>[OH-].[Na+]>[CH3:11][CH:10]1[CH2:9][C:8](=[O:12])[CH2:7][C:6](=[O:13])[CH2:5]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66769567HCID 66769567, compound

Product 1

HCID 4580955-Methylcyclohexane-1,3-dioneYield 49%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Hydroxy-6-methyl-4-oxo-cyclohex-1-enecarboxylic acid methyl ester (600 g, 3.30 mol) is dissolved in NaOH solution (5 M, 3 L) and the solution is refluxed for 2 h. After cooling to RT, the mixture is acidified with H2SO4 (5 M) to pH 7 and extracted with EtOAc (4×1 L). The organic phase is washed with brine and dried over anhydrous Na2SO4. The solvent is evaporated and the residue is recrystallized from hexane to give 5-methyl-cyclohexane-1,3-dione (200 g, 49% yield).

Workup

  1. temperaturethe solution is refluxed for 2 h
  2. extractionextracted with EtOAc (4×1 L)
  3. washThe organic phase is washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent is evaporated
  6. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-b7dd55fbf33e4075bec1ee2aa9ffedb3
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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