Ethylene Glycol → 2-Phenyl-1,3-dioxolane

HRID 1790993Notes

Reaction equation

HRID 1790993 reaction equation
O.[CH:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10](O)[CH2:11][OH:12]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[C:3]1([CH:2]2[O:12][CH2:11][CH2:10][O:9]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 240BenzaldehydeHCID 962Water

Product 1

HCID 702932-Phenyl-1,3-dioxolaneYield 89%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A 500-mL three-necked flask equipped with a reflux condenser having a Dean-Stark water trap was charged with 5.0 g of benzaldehyde, 29.3 g of ethylene glycol, 0.09 g of p-toluenesulfonic acid monohydrate and 250 mL of benzene, and the contents were refluxed for 21 h. The resultant reaction solution was allowed to stand for cooling and then washed with 50 mL of a saturated aqueous solution of sodium hydrogen carbonate and 50 mL of water. After vacuum-concentrating the organic phase, 6.3 g of the aimed 2-phenyl-1,3-dioxolane was obtained by vacuum distillation (89% yield).

Workup

  1. customA 500-mL three-necked flask equipped with a reflux condenser
  2. temperaturethe contents were refluxed for 21 h
  3. customThe resultant reaction solution
  4. temperaturefor cooling
  5. washwashed with 50 mL of a saturated aqueous solution of sodium hydrogen carbonate and 50 mL of water
  6. concentrationAfter vacuum-concentrating the organic phase

Sources & evidence

ORD record
ord-93912b0f9c4e4dadbfc0baf5ed7206e6
Source dataset
uspto-grants-2006_07
Patent number
US07071362B2

Reaction notes

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