Acetic Acid → Ethyl 3-(3-methylphenyl)-3-oxopropanoate

HRID 570584

Reaction equation

HRID 570584 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])=[O:11])[CH:7]=[CH:6][CH:5]=1.C[C:14]([OH:16])=[O:15].[C:17]1(C)C=CC=C[CH:18]=1>>[CH3:3][C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][CH:5]=1)[C:10]([CH2:12][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140Toluene2×HCID 114553-MethylacetophenoneHCID 24758Sodium hydride

Product 1

HCID 2760277Ethyl 3-(3-methylphenyl)-3-oxopropanoateYield 46.9%

Procedure

To a vigorously stirred suspension of NaH (564 mg, 48.5 mmol) and CO(OEt)2 (5.73 g, 48.5 mmol) in anhydrous toluene (50 ml) was added dropwise a solution of 3-methylacetophenone (4.33 g, 32.3 mmole) in toluene under reflux. The mixture was allowed to reflux and was stirred for 30 min after the addition was complete. When cooled to room temperature, the mixture was acidified with glacial AcOH. After ice-cold water was added, the mixture was extracted with toluene. The organic layer was dried over MgSO4, and evaporated. The residue was further chromatographed over silica gel by elution with CH2Cl2-n-haxane (3:2) to afford I-10-b as light-yellow liquid (3.13 g, 46.9%)

Workup

  1. temperatureunder reflux
  2. temperatureto reflux
  3. additionafter the addition
  4. additionAfter ice-cold water was added
  5. extractionthe mixture was extracted with toluene
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customThe residue was further chromatographed over silica gel by elution with CH2Cl2-n-haxane (3:2)

Sources & evidence

ORD record
ord-44ec3653270b4273974f36e6a4683cab
Source dataset
uspto-grants-2015_05
Patent number
US09023867B2

Linked notes

Loading…