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

HRID 1674677Notes

Reaction equation

HRID 1674677 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 (5-1) (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 hours, the mixture was concentrated. The residue was taken up in ethyl acetate and washed with saturated NaHCO3, H2O (2×), and brine. The organic layer was dried (Mg504), 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 (d, J=8.06 Hz, 2H), 7.59 (d, J=8.30 Hz, 2H), 5.85 (s, 1H), 4.13-4.05 (m, 4H).

Workup

  1. customThe flask was equipped with a Dean-Stark trap
  2. temperaturethe mixture heated to reflux
  3. concentrationthe mixture was concentrated
  4. washwashed with saturated NaHCO3, H2O (2×), and brine
  5. dry with materialThe organic layer was dried (Mg504)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9e82acbcdd5e4dc781765969ce26e917
Source dataset
uspto-grants-2011_08
Patent number
US08003643B2

Reaction notes

Loading…