Ethylene Glycol → 2-(3-Ethenylphenyl)-1,3-dioxolane

HRID 22590

Reaction equation

HRID 22590 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])=[CH2:2].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[C:5]([CH:6]2[O:13][CH2:12][CH2:11][O:7]2)[CH:8]=[CH:9][CH:10]=1)=[CH2:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 393903-VinylbenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 102413132-(3-Ethenylphenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-ethenylbenzaldehyde from Step 1 (3.77 g) and ethylene glycol (1.8 mL) in benzene (40 mL) was added p-toluenesulfonic acid monohydrate (100 mg). The reaction mixture was heated to reflux for 6 hours. The water produced by the reaction was collected in a Dean-Stark trap. The reaction was allowed to cool to room temperature. The reaction was diluted with NH4OAc buffer and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated. Flash chromatography of the residue using 15% diethyl ether in hexane afforded the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. customwas collected in a Dean-Stark trap
  4. additionThe reaction was diluted with NH4OAc buffer
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-587e164d49264c9ebf8e8b4e81762f69
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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