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

HRID 1678751Notes

Reaction equation

HRID 1678751 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:8]1[CH2:11][CH2:12][O:13][CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 660424-Cyanobenzaldehyde

Product 1

HCID 27784284-(1,3-Dioxolan-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-cyanobenzaldehyde (20.0 g, 152.5 mmol) and ethylene glycol (25.5 mL, 457.5 mmol) in toluene (250 mL) was added p-toluenesulfonic acid (300 mg). The flask was equipped with a Dean-Stark trap and the mixture heated to reflux. After 5 hr the mixture was concentrated. The residue was taken up in ethyl acetate and washed with saturated NaHCO3, water (2×), and brine. The organic layer was dried (MgSO4), filtered, and concentrated to give 4-(1,3-dioxolan-2-yl)benzonitrile as a clear oil which solidified under vacuum: 1H-NMR (500 MHz, CDCl3): δ 7.67 (2H, d, J=8.06 Hz), 7.59 (2H, d, J=8.30 Hz), 5.85 (1H, s), 4.13-4.05 (4H, m).

Workup

  1. customThe flask was equipped with a Dean-Stark trap
  2. temperaturethe mixture heated to reflux
  3. concentrationAfter 5 hr the mixture was concentrated
  4. washwashed with saturated NaHCO3, water (2×), and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec5ddc76275c4531978fe6ee76a89845
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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