Ethylene Glycol → 4-(1,3-Dioxolan-2-yl)benzaldehyde

HRID 1012368Notes

Reaction equation

HRID 1012368 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:1]2[O:13][CH2:12][CH2:11][O:10]2)=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12173TerephthalaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 118299884-(1,3-Dioxolan-2-yl)benzaldehydeYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 134 g of terephthalaldehyde and 62 g of ethylene glycol, was added 400 mL of toluene, and then was added thereto 2 g of p-toluenesulfonic acid, to conduct dehydration reaction under azeotropic conditions. After the time when the reaction of water stopped in the reaction, the reaction liquid was heated under reflux for another 2 hours, followed by cooling. The resultant reaction liquid was poured into an aqueous sodium bicarbonate solution. The organic phase was concentrated, and then purified by silica gel column chromatography (yield amount 122 g, and yield 68.5%).

Workup

  1. additionwas added
  2. customdehydration reaction under azeotropic conditions
  3. customstopped in the reaction
  4. customthe reaction liquid
  5. temperaturewas heated
  6. temperatureunder reflux for another 2 hours
  7. temperatureby cooling
  8. customThe resultant reaction liquid
  9. concentrationThe organic phase was concentrated
  10. custompurified by silica gel column chromatography (yield amount 122 g, and yield 68.5%)

Sources & evidence

ORD record
ord-b32dee2489974b3abde46615685393ef
Source dataset
uspto-grants-2011_07
Patent number
US07977491B2

Reaction notes

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