Ethylene Glycol → 2-(5-Chloro-2-nitrophenyl)-1,3-dioxolane

HRID 256178

Reaction equation

HRID 256178 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:13](O)[CH2:14][OH:15].C1C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]2[O:15][CH2:14][CH2:13][O:8]2)[CH:9]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 811235-Chloro-2-nitrobenzaldehyde

Product 1

HCID 2673852-(5-Chloro-2-nitrophenyl)-1,3-dioxolaneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared as described by D. E. O'Brien et al, J. Het. Chem., 7, 102 (1970) as follows. A mixture of 5-chloro-2-nitrobenzaldehyde (18.3 g, 0.1 mole), ethylene glycol (7.0 g, 0.11 mole) p-toluenesulfonic acid (0.5 g) and benzene (850 mL) was stirred and refluxed with continuous removal of water via a Dean and Stark trap for 24 hours. The solvent was removed, the residue dissolved in dichloromethane and filtered through a plug of silica gel (6" deep). Evaporation of the solvent afforded 2-(5-chloro-2-nitrophenyl)-1,3-dioxolane (21.8 g, 97%) as an oil.

Workup

  1. customPrepared
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in dichloromethane
  4. filtrationfiltered through a plug of silica gel (6" deep)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f59f10b2b24d46e0b5a53c3c2bb67170
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Linked notes

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