Trifluoroacetic acid → 1-(3-Nitropropyl)-4-octylbenzene
Reaction equation
[N+:1]([CH2:4][CH2:5][CH: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].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[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
- 0 °C
Procedure
3-Nitro-1-(4-octylphenyl)propan-1-ol (30 g) and trifluoroacetic acid (47 mL) are charged into a round bottom flask equipped with a calcium chloride guard tube. The mixture is cooled to 0° C., triethylsilane (32.5 mL) is added, and the mixture is stirred overnight at room temperature. The mass is poured onto crushed ice (200 g) and the mixture is extracted with ethyl acetate (2×200 mL). The combined organic layer is dried over sodium sulphate and concentrated under reduced pressure, to give the crude as a color liquid. The crude obtained is purified by silica gel column chromatography (100-200 mesh, 500 g) using 5% ethyl acetate in hexane as the eluent, and the eluted fraction containing the desired compound are pooled, evaporated under reduced pressure to give the title compound. Yield: 19.8 g.
Workup
- customequipped with a calcium chloride guard tube
- additionThe mass is poured
- extractionthe mixture is extracted with ethyl acetate (2×200 mL)
- dry with materialThe combined organic layer is dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- customto give the crude as a color liquid
- customThe crude obtained
- customis purified by silica gel column chromatography (100-200 mesh, 500 g)
- additionthe eluted fraction containing the desired compound
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-54b3c592db16497db39927c690587f90
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216943B2
Reaction notes
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