Ethanol → Ethyl 4-(4-methoxy-3-methylphenyl)-4-oxobutanoate

HRID 1795575Notes

Reaction equation

HRID 1795575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][C:4]=1[CH3:16].[OH-].[Na+].[CH2:19](O)[CH3:20]>OS(O)(=O)=O.O>[CH2:19]([O:13][C:12](=[O:14])[CH2:11][CH2:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:16])[CH:5]=1)=[O:15])[CH3:20]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 31635964-(4-Methoxy-3-methylphenyl)-4-oxobutanoic acid2×

Product 1

HCID 10467279Ethyl 4-(4-methoxy-3-methylphenyl)-4-oxobutanoateYield 84%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-(4-methoxy-3-methylphenyl)-4-oxobutyric acid (Compound 2, 21.75 g, 98.0 mmol) in absolute ethanol (200 mL) was added 10 drops of concentrated H2SO4. The resulting solution was refluxed for 3 days, then cooled to room temperature, treated with 30 mL of NaOH 2 N, diluted with 50 mL of water, and extracted 3 times with EtOAc. The combined organic layers were washed with brine, and dried over MgSO4, and filtered. The solvent was removed to afford 20.6 g (84%) of the title compound as a yellow solid.

Workup

  1. temperatureThe resulting solution was refluxed for 3 days
  2. extractionextracted 3 times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-a0f8f8d52882438f95a4e4bce39b9927
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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