Ethylene Glycol → 2-(2-Nitroethyl)-1,3-dioxolane

HRID 606615Notes

Reaction equation

HRID 606615 reaction equation
[N+:1]([CH2:4][CH2:5][CH:6]=[O:7])([O-:3])=[O:2].[CH2:8](O)[CH2:9][OH:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([CH2:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 64536753-Nitropropanal

Product 1

HCID 108880592-(2-Nitroethyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask fitted with a Dean-Stark trap and reflux condenser, a solution of 3-nitro-propionaldehyde (138 g, 1.34 mol) in toluene (1 L) was treated with ethylene glycol (83 g, 1.34 mol) and p-toluenesulfonic acid monohydrate (5.0 g, 26 mmol). The mixture was heated at reflux, open to air, for 4 h, and then cooled to rt. A black residue was removed by paper filtration. The filtrate was washed with satd. aq. NaHCO3 (250 mL) and brine (3×100 mL). Charcoal and MgSO4 were added, and the resulting suspension was stirred for 1 h. Filtration and concentration of the filtrate gave the title compound, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): 5.03 (t, J=3.6, 1H), 4.50 (t, J=6.8, 2H), 4.05-3.90 (m, 2H), 3.90-3.80 (m, 2H), 2.44 (td, J=6.8, 3.6, 2H).

Workup

  1. customIn a flask fitted with a Dean-Stark trap
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureat reflux, open to air, for 4 h
  5. customA black residue was removed by paper filtration
  6. washThe filtrate was washed with satd
  7. additionCharcoal and MgSO4 were added
  8. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-5b065a9b6fd4416d91f7671c654b5fb2
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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