Acetic Acid → HCID 59845732, compound

HRID 418476Notes

Reaction equation

HRID 418476 reaction equation
[Na].[N+:2]([CH3:5])([O-:4])=[O:3].[CH3:6][C:7]1([CH3:14])[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1.C(O)(=O)C>C(O)C.O>[CH3:6][C:7]1([CH3:14])[CH2:12][CH2:11][C:10]([CH2:5][N+:2]([O-:4])=[O:3])([OH:13])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 5360545Sodium

Product 1

HCID 59845732HCID 59845732, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of sodium (0.2 g, 0.009 mol) and ethanol (5 mL, 0.08 mol) was added a solution of nitromethane (0.77 g, 0.013 mol) and 4,4-dimethyl-cyclohexanone (1 g, 0.008 mol) in ethanol (1 mL) dropwise. The mixture was stirred at room temperature for 4 hours. Acetic acid (2 mL) and water (10 mL) were added and the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL), washed with brine (30 mL×3), dried over sodium sulfate, and purified by flash chromatography to afford the desired product as a clear oil. (1.5 g, 90%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with brine (30 mL×3)
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-433148dae33f45518171ee7dec51bcb2
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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