Ethylene Glycol → 2-(4-Nitrophenyl)-1,3-dioxolane

HRID 888057Notes

Reaction equation

HRID 888057 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[O:14][CH2:13][CH2:12][O:9]2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 5414-NitrobenzaldehydeHCID 6101p-Toluenesulfonic acid

Product 1

HCID 2667962-(4-Nitrophenyl)-1,3-dioxolaneYield 92.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a 3-neck round-bottom flask equipped with Dean-Stark apparatus, reflux condenser and mechanical stirrer, p-nitrobenzaldehyde (101.5 g, 672 mmol), ethylene glycol (112 mL, 2.0 mol), and p-toluene sulfonic acid (12.8 g, 67.2 mmol, 10% mol) were suspended in toluene (800 mL) and then heated at 120° C. for 4 hours. The reaction mixture was cooled to room temperature and the toluene was removed under reduced pressure. Saturated aqueous sodium bicarbonate solution (800 mL) was added, and the resulting slurry was stirred at room temperature for 15 minutes, and then filtered and dried under vacuum to give the title compound (121.8 g) as a solid. 1H NMR (DMSO-d6): δ=8.12 (d, 2H), 7.59 (d 2H), 5.78 (s, 1H), 3.8-4.0 (m, 4H).

Workup

  1. customIn a 3-neck round-bottom flask equipped with Dean-Stark apparatus
  2. temperaturereflux condenser and mechanical stirrer
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe toluene was removed under reduced pressure
  5. additionSaturated aqueous sodium bicarbonate solution (800 mL) was added
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5197c77e0b784db8b4ff4c6f81fbeb70
Source dataset
uspto-grants-2012_08
Patent number
US08247564B2

Reaction notes

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