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

HRID 1487191

Reaction equation

HRID 1487191 reaction equation
O.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=[O:9].[CH2:14](O)[CH2:15][OH:16].ClCCl>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:8]2[O:16][CH2:15][CH2:14][O:9]2)[CH:10]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6344DichloromethaneHCID 811235-Chloro-2-nitrobenzaldehyde

Product 1

HCID 2673852-(5-Chloro-2-nitrophenyl)-1,3-dioxolaneYield 90.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In a flask equipped with a Dean-Stark water separator, 5-chloro-2-nitrobenzaldehyde (12.0 g, 64.7 mmol), ethylene glycol (8.0 g, 129.3 mmol) and p-toluenesulfonic acid (0.2 g) were dissolved in toluene (150 mL). The mixture was stirred at reflux for 8 hours. Dichloromethane was added and the organic phase was washed with saturated sodium bicarbonate and brine, then dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 2-(5-chloro-2-nitrophenyl)-1,3-dioxolane (13.4 g, yield 90.0%).

Workup

  1. temperatureat reflux for 8 hours
  2. washthe organic phase was washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3628717df63f43608aef6ebf813b0d85
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Linked notes

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