Ethylene Glycol → 2-Methyl-2-(3-nitropropyl)-1,3-dioxolane

HRID 1044732Notes

Reaction equation

HRID 1044732 reaction equation
N#N.[N+:3]([CH2:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])([O-:5])=[O:4].[CH2:12](O)[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH3:10][C:9]1([CH2:8][CH2:7][CH2:6][N+:3]([O-:5])=[O:4])[O:14][CH2:13][CH2:12][O:11]1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 42950035-Nitro-2-pentanone

Product 1

HCID 6383462-Methyl-2-(3-nitropropyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus and under inert atmosphere (N2), crude 5-nitro-pentan-2-one (28.53 mmol) was dissolved in dry toluene (28 mL). Ethylene glycol (10.2 mL, 183.02 mmol) and p-TsOH (696 mg, 3.66 mmol) were added and the reaction mixture stirred at 120° C. for 5 h. The reaction mixture was then cooled down to rt and sat. aq. NaHCO3 was added. The layers were separated and the org. layer washed with brine (2×), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 4:1) to give the title compound as a pale brown oil. TLC:rf (4:1 hept-EA)=0.21.

Workup

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was then cooled down to rt
  3. customThe layers were separated
  4. washlayer washed with brine (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by FC (hept-EA, 4:1)

Sources & evidence

ORD record
ord-0a809eeaae9348cbba118f0bebd2473b
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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