Diethyl 2-(2-(4-nitrophenyl)acetyl)malonate → 1-(4-Nitrophenyl)propan-2-one
Reaction equation
C(OC(=O)[CH:5]([C:11](=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)C(OCC)=O)C>CS(C)=O.O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11](=[O:22])[CH3:5])=[CH:18][CH:17]=1)([O-:21])=[O:20]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
2-[2-(4-Nitro-phenyl)-acetyl]-malonic acid diethyl ester (1.4 g) was taken up in a mixture of DMSO (8 ml) and water (4 ml) and heated at 150° C. with stirring for 10 hr. The product was extracted with ethyl acetate (50 ml). The organic layer was washed with water, aqueous sodium bicarbonate solution and brine. The organic layer was then dried over sodium sulphate, filtered and evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (6:94) as eluent yielded 1-(4-nitro-phenyl)-propan-2-one (160 mg, 24%).