Acetic Acid → 1-(3,4-Dimethoxyphenyl)butane-1,3-dione

HRID 719261

Reaction equation

HRID 719261 reaction equation
[H-].[Na+].C1CCCCC1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19](=[O:21])[CH3:20])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].[C:22](O)(=[O:24])[CH3:23]>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19](=[O:21])[CH2:20][C:22](=[O:24])[CH3:23])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8078CyclohexaneHCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 24758Sodium hydride

Product 1

HCID 3680601-(3,4-Dimethoxyphenyl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.9 g of sodium hydride were initially introduced into 150 ml of cyclohexane, and a solution of 15 g of 1-(3,4-dimethoxyphenyl)ethanone in 16.3 ml of ethyl acetate was added. The reaction solution was boiled at 80° C. for 1 h, after which acetic acid was added and the whole was extracted with MTB-ether. The MTB-ether phase was dried over magnesium sulfate and subjected to rotary evaporation. The residue was chromatographed through silica gel (ethyl acetate/heptane 1/6). The following was obtained: 41 C12H14O4 (222.24); MS (ESI) 223 (M+H)

Workup

  1. customfor 1 h
  2. extractionthe whole was extracted with MTB-ether
  3. dry with materialThe MTB-ether phase was dried over magnesium sulfate
  4. customsubjected to rotary evaporation
  5. customThe residue was chromatographed through silica gel (ethyl acetate/heptane 1/6)
  6. customThe following was obtained

Sources & evidence

ORD record
ord-744a70eef3984d2fb590d3ed12233ef3
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Linked notes

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