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

HRID 444950Notes

Reaction equation

HRID 444950 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).

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-a7e68a39351b4eb7b28a08ce8c8acea0
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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