Lithium Hydroxide → 1,1,1-Trifluoro-2-methyl-3-nitropropan-2-ol

HRID 887885Notes

Reaction equation

HRID 887885 reaction equation
[Li+].[OH-].[N+:3]([CH3:6])([O-:5])=[O:4].[F:7][C:8]([F:13])([F:12])[C:9](=[O:11])[CH3:10].[O-]S([O-])(=O)=O.[Mg+2]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C(OCC)C.O>[F:7][C:8]([F:13])([F:12])[C:9]([CH3:10])([OH:11])[CH2:6][N+:3]([O-:5])=[O:4]

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 6375NitromethaneHCID 9871Methyl trifluoromethyl ketoneHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 136207581,1,1-Trifluoro-2-methyl-3-nitropropan-2-ol

Reagents, catalysts & solvents 3

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
22.5 °C

Procedure

To LiOH (0.193 g, 8.06 mmol) in a 3-neck roundbottom flask was added water (25 ml), nitromethane (3.76 ml, 81 mmol) and trifluoroacetone (7.95 ml, 89 mmol). Cetyltrimethylammonium chloride (3.8 g, 10.88 mmol) and MgSO4 (1.9 g, 16.12 mmol) were added and the resulting yellow solution stirred at 20-25° C. for 2 days. The reaction mixture was poured into diethyl ether (120 ml) and washed with water (3×200 ml) and brine (1×100 ml). The organic portion was dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow liquid. 1H NMR (CDCl3, 400 MHz): δ 4.7 (1H, d), δ 4.5 (1H, d), δ 3.7 (1H, broad), δ 1.6 (3H, s). Step 2: 3-Amino-1,1,1-trifluoro-2-methylpropan-2-ol hydrochloride

Workup

  1. washwashed with water (3×200 ml) and brine (1×100 ml)
  2. dry with materialThe organic portion was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a28ad1ded3014688b2feacfb6c9efe72
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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