Hydrochloric Acid → 1,1,1-Trifluoro-3-nitro-2-pentanol
Reaction equation
C(O[CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6])C.C(=O)([O-])[O-].[K+].[K+].Cl.[N+:17]([CH2:20][CH2:21][CH3:22])([O-:19])=[O:18]>>[F:8][C:5]([F:6])([F:7])[CH:4]([OH:9])[CH:20]([N+:17]([O-:19])=[O:18])[CH2:21][CH3:22]Participants
5
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 1-nitropropane (10 mL), trifluoroacetaldehyde ethyl hemiacetal (20.2 mL), and potassium carbonate (15.4 g) was stirred at 25° C. for 48 h. The solution was made acidic by addition of 1N hydrochloric acid and the product extracted into dichloromethane. The solution was dried (MgSO4) and the solvent evaporated to give an oil, which was distilled (60° C., 133 Pa) to provide 1,1,1-trifluoro-3-nitro-2-pentanol (15 g) as a mixture of diastereoisomers; MS: m/z=188(M+1).
Workup
- extractionthe product extracted into dichloromethane
- dry with materialThe solution was dried (MgSO4)
- customthe solvent evaporated
- customto give an oil, which
- distillationwas distilled (60° C., 133 Pa)
Sources & evidence
- ORD record
- ord-1bb77e1f17054698ae1a48afa7fc32fa
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521179
Reaction notes
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