Water → 1-(3-Nitropropyl)-4-octylbenzene
Reaction equation
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)=O)([O-:3])=[O:2].C([SiH](CC)CC)C.O>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[N+:1]([CH2:4][CH2:5][CH2:6][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:13]=1)([O-:3])=[O:2]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
3-Nitro-1-(4-octylphenyl)propan-1-one (37 g) and dichloromethane (185 mL) are charged into a round bottom flask at 25-30° C. and stirred. Triethylsilane (36.87 g) is charged into the flask and the reaction mixture is cooled to 0-5° C. Titanium tetrachloride (28.9 g) in dichloromethane (185 mL) is added to the reaction mixture over the period of 30 minutes at temperature below 5° C. and the reaction mixtures is stirred at a temperature of 25-30° C. for about 1 hour. The reaction mixture is added to water (370 mL) precooled to 0-5° C., stirred, and the organic layer is separated. The organic layer is washed with aq. sodium bicarbonate (2×370 mL), followed by water (370 mL), and brine solution (370 mL). The organic layer is dried over sodium sulphate and evaporated under reduced pressure at about 45° C. to give 64.0 g of the title compound.
Workup
- customthe reaction mixtures
- stirringis stirred at a temperature of 25-30° C. for about 1 hour
- customprecooled to 0-5° C.
- stirringstirred
- customthe organic layer is separated
- washThe organic layer is washed with aq. sodium bicarbonate (2×370 mL)
- dry with materialThe organic layer is dried over sodium sulphate
- customevaporated under reduced pressure at about 45° C.
Sources & evidence
- ORD record
- ord-e00cda740f85422c9e4171359d65d1b8
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216943B2
Reaction notes
Loading…