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

HRID 852879Notes

Reaction equation

HRID 852879 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[CH2:12](O)[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]2[O:14][CH2:13][CH2:12][O:8]2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 74493-Nitrobenzaldehyde

Product 1

HCID 2406102-(3-nitrophenyl)-1,3-dioxolaneYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of m-nitrobenzaldehyde 69d (20 g, 0.13 mol), ethylene glycol (9.0 g, 0.15 mol) and p-TsOH (catalytic amount) in toluene (50 mL) was refluxed under a Dean-Stark trap for 12 hr. The solution was then cooled to room temperature, diluted with toluene (20 mL) and washed with NaOH solution (1 M, 20 mL), water, brine and then dried with MgSO4. Evaporation of the solvent under reduced pressure gave 2-(3-Nitro-phenyl)-[1,3]dioxolane (24 g, 95%): 1H NMR (CDCl3) δ 4.11 (d of mult, ethylenedioxy, 4H), 5.78 (s, 1H), 7.56 (t, J=8 Hz, 1H), 7.80 (d of mult, J=8 Hz), 8.22 (d of mult., 1H), 8.35 (m, 1H). 13C NMR (CDCl3) δ 148.3, 140.5, 132.8, 129.5, 124.1, 121.7, 102.3, 65.6.

Workup

  1. washwashed with NaOH solution (1 M, 20 mL), water, brine
  2. dry with materialdried with MgSO4
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e6748671cb8a4e9da86c764d50beb5cf
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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