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

HRID 2080120Notes

Reaction equation

HRID 2080120 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[CH2:11](O)[CH2:12][OH:13].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:2]1[CH2:11][CH2:12][O:13][CH:1]1[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 660424-CyanobenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileYield 94.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

4-Formyl-benzonitrile (3.00 g, 22.9 mmol), ethane-1,2-diol (6.38 mL, 115 mmol) and toluene-4-sulfonic acid monohydrate (197 mg, 1.15 mmol) were dissolved in toluene (60 mL), and the solution was stirred under reflux for 10 hours. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (3.78 g, 21.6 mmol, 94%) was obtained as a white solid.

Workup

  1. temperatureunder reflux for 10 hours
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-f630e6e0c4904ed4b67148f5b93227a5
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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