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

반응식

[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]

참가 물질

반응물 4

HCID 176Acetic Acid

HCID 1140Toluene2회

HCID 114553-Methylacetophenone

HCID 24758Sodium hydride

생성물 1

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

실험 절차

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%)