Sulfuric Acid → 2-Acetyl-1,3-cyclohexanedione

HRID 2366499

Reaction equation

HRID 2366499 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C([O:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=1)(=O)C.[OH:16]S(O)(=O)=O.Cl[CH:22](Cl)[CH3:23]>>[C:22]([CH:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH2:14][C:9]1=[O:8])(=[O:16])[CH3:23]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 63651,1-DichloroethaneHCID 27554433-Acetoxy-2-cyclohexen-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1381042-Acetyl-1,3-cyclohexanedioneYield 59%

Procedure

According to Scheme 4 Step 2: AlCl3 (26.5 mmol, 3.53 g) was added to a solution of 3-oxocyclohex-1-enyl acetate (13.2 mmol, 2.04 g) in dichloroethane (10 mL) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured onto a solution of H2SO4 in ice. The aqueous phase was extracted with CHCl3 (50 mL). The organic phase was washed with water, dried over Na2SO4, was filtered and was concentrated to yield 2-acetylcyclohexane-1,3-dione (7.78 mmol, 1.20 g, 59%) as a yellow oil.

Workup

  1. extractionThe aqueous phase was extracted with CHCl3 (50 mL)
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationwas filtered
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-411f976d5d964e97b0e5089fb4fd3785
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Linked notes

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