2-Propylaniline → 2-(4-Amino-3-propyl-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol
Reaction equation
[CH2:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH2:2][CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.O.O.[F:26][C:27]([F:35])([F:34])[C:28]([C:30]([F:33])([F:32])[F:31])=[O:29]>C(OCC)(=O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([C:28]([OH:29])([C:30]([F:33])([F:32])[F:31])[C:27]([F:35])([F:34])[F:26])=[CH:10][C:4]=1[CH2:1][CH2:2][CH3:3]Participants
5
Conditions
- Temperature
- 130 °C
Procedure
2-Propylaniline (111 mmol, 15 g), p-toluenesulfonic acid monohydrate (11.09 mmol, 2.110 g) and hexafluoroacetone trihydrate (111 mmol, 24.41 g) were combined and heated to 130° C. for 3 hours. The mixture was allowed to cool and diluted with ethyl acetate (250 mL). The solution was washed with sodium bicarbonate solution (3×100 mL), the organic phase was dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was allowed to crystallise overnight. The crystals were collected by filtration, washed with heptane (100 mL) and dried under vacuum to afford the title compound (14.3 g).
Workup
- temperatureto cool
- washThe solution was washed with sodium bicarbonate solution (3×100 mL)
- dry with materialthe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customto crystallise overnight
- filtrationThe crystals were collected by filtration
- washwashed with heptane (100 mL)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-3141d71782554fceb69ea9b5d4d50312
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357679B2
Reaction notes
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