Ethylene Glycol → 3-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile

HRID 2070992Notes

Reaction equation

HRID 2070992 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].[CH2:12](O)[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1>C([O-])(O)=O.[Na+]>[CH3:2][C:1]1([C:4]2[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=2)[C:7]#[N:8])[O:14][CH2:13][CH2:12][O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 802223-Acetylbenzonitrile

Product 1

HCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileYield 79.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A stirred solution of 3-acetylbenzonitrile (1.05 g, 7.2 mmol), ethylene glycol (0.81 mL, 14.5 mmol) and TsOH (0.65 g, 7.2 mmol) was heated at reflux with a Dean-Stark for 15 h during which time the reaction became dark brown suspension. The reaction mixture was cooled to room temperature and diluted with saturated aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (10% EtOAc in hexanes) to provide 3-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (1.08 g, 79%).

Workup

  1. temperatureat reflux with a Dean-Stark for 15 h during which time the reaction
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-283c9e58ce4c45b2a8ae5d105c891639
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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