Diethyl Ether → 2,2-Dinitro-3-phenylbutane
Reaction equation
[N+:1]([C:4]([CH3:12])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].CCOCC.[CH3:18][Li].[N+:20](C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O)([O-:22])=[O:21]>C1COCC1>[N+:1]([C:4]([N+:20]([O-:22])=[O:21])([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:18])[CH3:12])([O-:3])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a solution of 4.03 g (0.025 mol) of 2-nitro-1-phenyl-1-propene dissolved in 30 ml of dry THF (cooled to -40° C. with an acetronitrile-dry ice bath) and under a positive nitrogen atmosphere was added with stirring 22 ml (0.05 mol) of a 5% ether solution of methyllithium. The resulting solution was stirred for 1 h at -40° C. followed by the addition of 4.9 g (0.025 mol) of tetranitromethane. The solution was then allowed to warm to room temperature and stirred an additional hour. The resulting product was isolated and purified as described in Example 1 above, yielding 3.4 g (60% yield) of an analytically pure white crystalline product, mp 76°-78° C. A similar procedure was used for the preparation of derivatives wherein R3 (see structure above or scheme) was CH3 (CH2)3 and R2 was H and wherein R3 was CH3 and R2 was CH3 (see scheme).
Workup
- additionwas added
- temperatureto warm to room temperature
- stirringstirred an additional hour
- customThe resulting product was isolated
- custompurified
- customyielding 3.4 g (60% yield) of an analytically pure white crystalline product, mp 76°-78° C
- customA similar procedure was used for the preparation of derivatives wherein R3 (see structure above or scheme)
Sources & evidence
- ORD record
- ord-73d919031ab6434b8f17b1b6c3007790
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220804
Reaction notes
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