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

HRID 1734009Notes

Reaction equation

HRID 1734009 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].B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[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

6

Reactant 4

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 802223-AcetylbenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileYield 99.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-acetylbenzonitrile (50.0 g), ethylene glycol (34.0 g) and boron trifluoride etherate (1 ml) in benzene (200 ml) was heated at 100° C. by means of a Dean-Stark apparatus for 5 hours. After cooling, a saturated aqueous sodium hydrogencarbonate solution (200 ml) was added. The benzene layer was collected and then dried with sodium sulfate. The solvent was removed under reduced pressure to afford 3-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (65.0 g) (oil).

Workup

  1. temperatureAfter cooling
  2. customThe benzene layer was collected
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5083d86795b24b1581068d6435b3d646
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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