Ethanone, 1-(4-Methyl-2-nitrophenyl) synthesis
- Product Name:Ethanone, 1-(4-Methyl-2-nitrophenyl)
- CAS Number:155694-84-1
- Molecular formula:C9H9NO3
- Molecular Weight:179.17
1449199-73-8
155694-84-1
Example 22 Preparation of 1-(4-methyl-2-nitrophenyl)ethan-1-one (C84): In a reaction flask was added 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (11.4 g, 64.3 mmol), dichloromethane (292 mL) and methanol (29.2 mL). The reaction mixture was cooled to -78° C. Ozone was passed into the reaction mixture and stirred at -78° C for 3 hours. Subsequently, the reaction mixture was purged with nitrogen to remove unreacted ozone. Dimethyl sulfide (14.0 mL, 189 mmol) was added, and the reaction mixture was stirred and gradually warmed to room temperature overnight. Upon completion of the reaction, the mixture was concentrated. Purification by fast column chromatography using ethyl acetate/hexane as eluent afforded the target product 1-(4-methyl-2-nitrophenyl)ethanone as an oil (8.90 g, 70% yield).1H NMR (300 MHz, CDCl3) δ 7.85 (dd, J = 1.7, 0.8 Hz, 1H), 7.50 (ddd, J = 7.8, 1.7, 0.8 Hz), 7.50 (ddd, J = 7.8, 0.8 Hz). 1.7, 0.8 Hz, 1H), 7.35 (dd, J = 7.7, 0.9 Hz, 1H), 2.53 (s, 3H), 2.48 (s, 3H).
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155694-84-1
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Yield:155694-84-1 70%
Reaction Conditions:
Stage #1: 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzenewith ozone in methanol;dichloromethane at -78; for 3 h;
Stage #2: with dimethylsulfide in methanol;dichloromethane at 20;
Steps:
22 Preparation of 1-(4-methyl-2-nitrophenyl)ethan-1-one (C84)
Example 22
Preparation of 1-(4-methyl-2-nitrophenyl)ethan-1-one (C84)
To a reaction flask were added 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (11.4 g, 64.3 mmol), dichloromethane (292 mL), and methanol (29.2 mL).
The reaction mixture was cooled to -78° C.
Ozone was bubbled into the reaction mixture, and the reaction mixture was stirred at -78° C. for 3 hours.
The reaction mixture was flushed with nitrogen.
Dimethylsulfide (14.0 mL, 189 mmol) was added, and the reaction mixture was allowed to stir and warm to room temperature overnight.
The reaction was concentrated.
Purification by flash column chromatography using ethyl acetate/hexanes as eluent provided the title compound as an oil (8.90 g, 70%): 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, J=1.7, 0.8 Hz, 1H), 7.50 (ddd, J=7.8, 1.7, 0.8 Hz, 1H), 7.35 (dd, J=7.7, 0.9 Hz, 1H), 2.53 (s, 3H), 2.48 (s, 3H).
References:
US2017/64962,2017,A1 Location in patent:Paragraph 0627; 0628