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

HRID 250527Notes

Reaction equation

HRID 250527 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].O.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 660424-CyanobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Cyanobenzaldehyde (500 mg, 3.81 mmol), ethylene glycol (828 mg, 13.34 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed in toluene (25 mL) overnight in a Dean-Stark apparatus. The reaction mixture was then concentrated and the residue dissolved in chloroform (50 ml) and washed with saturated sodium bicarbonate solution (2×25 mL) and brine (1×25 mL). The organic phase was then dried (Na2SO4) and evaporated to give 4-(1,3-dioxolan-2-yl)benzenecarbonitrile (40) as an oil which solidified to a white solid (633 mg, 95%). 1H NMR (CDCl3, 300 MHz): δ 4.04, t (1.8 Hz), OCH2; 4.07, t (2.0 Hz), OCH2; 5.82, s, H2; 7.64, d (1.4 Hz), 2×ArH; 7.73, d (1.3 Hz), 2×ArH. ESI (+ve) MS: m/z 176 (M+H, 12%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue dissolved in chloroform (50 ml)
  3. washwashed with saturated sodium bicarbonate solution (2×25 mL) and brine (1×25 mL)
  4. dry with materialThe organic phase was then dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d5606cd1ddcd40338072b7f00fb5a87e
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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