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

HRID 256181Notes

Reaction equation

HRID 256181 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].C1C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[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

6

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 74493-Nitrobenzaldehyde

Product 1

HCID 2406102-(3-nitrophenyl)-1,3-dioxolaneYield 101.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-nitrobenzaldehyde (100 g, 0.66 mole), ethylene glycol (49.3 g, 0.7 mole) and p-toluenesulfonic acid (0.8 g) and benzene (1 L) was heated at reflux with continuous removal of water via a Dean and Stark trap. After 4 hours, the mixture was cooled, filtered through a pad of neutral alumina and concentrated in vacuo to afford 2-(3-nitrophenyl)-1,3-dioxolane (130.4 g, 100%) as an amber oil used without further purification below.

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was cooled
  3. filtrationfiltered through a pad of neutral alumina
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b4ac652bfc34523811da326226c9728
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Reaction notes

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