Nitromethane → HCID 49764651, compound

HRID 384984Notes

Reaction equation

HRID 384984 reaction equation
[OH-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[CH3:7][CH:8]([CH2:11][CH2:12][CH3:13])[CH:9]=[O:10]>O.C(O)C>[CH3:7][CH:8]([CH2:11][CH2:12][CH3:13])[CH:9]([OH:10])[CH2:6][N+:3]([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 312452-Methylpentaldehyde

Product 1

HCID 49764651HCID 49764651, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

After dissolving 7.0 g of sodium hydroxide in 50 ml of water and 50 ml of ethanol at 4° C., 10.7 g of nitromethane and 10.0 g of 2-methylpentanal were added thereto. The temperature of the solution was allowed to rise to room temperature, and the solution was stirred for two hours. 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 13.3 g of 3-methyl-1-nitro-2-hexanol (yield: 94.2%).

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-dba9c7fe2752485480c89f04963c0e80
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

Loading…