Ethanol → HCID 49764771, compound

HRID 384985Notes

Reaction equation

HRID 384985 reaction equation
[OH-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[CH3:7][CH:8]([CH2:11][CH2:12][CH2:13]C)[CH:9]=[O:10].[CH2:15](O)C>O>[CH3:7][CH:8]([CH2:11][CH:12]([CH3:13])[CH3:15])[CH:9]([OH:10])[CH2:6][N+:3]([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 1025152-Methylhexanal

Product 1

HCID 49764771HCID 49764771, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After dissolving 5.0 g of sodium hydroxide in 25 ml of water and 25 ml of ethanol at 4° C., 7.7 g of nitromethane and 7.2 g of 2,5-dimethylpentanal were added thereto. The temperature of the solution was allowed to rise to room temperature, and the solution was stirred for an hour. After concentrating the ethanol under reduced pressure, the solution was neutralized with 1 mol/l of hydrochloric acid so that the pH of the solution was approximately 7. Ethyl acetate was added to the solution, and the organic layer was washed with saturated saline. The organic layer was dried with magnesium sulfate and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=8/1), thereby obtaining 9.0 g of 3,5-dimethyl-1-nitro-2-hexanol (yield: 81.4%).

Workup

  1. customto rise to room temperature
  2. concentrationAfter concentrating the ethanol under reduced pressure
  3. additionEthyl acetate was added to the solution
  4. washthe organic layer was washed with saturated saline
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-d8d7a7bd7ab64489838284808276bed5
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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