Ethylene Glycol → HCID 11159613, compound

HRID 1354409Notes

Reaction equation

HRID 1354409 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[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:7]1[CH2:11][CH2:12][O:13][CH:6]1[C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 90670m-Formylbenzonitrile

Product 1

HCID 11159613HCID 11159613, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-cyanobenzaldehyde (9.81 g), ethylene glycol (9.31 g), p-toluenesulfonic acid monohydrate (0.07 g) and toluene (200 ml) was heated under reflux for 15 hrs., while removing generated water with a Dean-Stark trap. After cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. This solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 3-(1,3-dioxolan-2-yl)benzonitrile (13.1 g, yield 100%) as a colorless oil. NMR (CDCl3) δ: 4.01–4.17 (4H, m), 5.83 (1H, s), 4.50 (1H, t, J=7.6 Hz), 7.63–7.74 (2H, m), 7.80 (1H, t, J=1.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. custom, while removing
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated
  6. additionthe residue was diluted with ethyl acetate
  7. washThis solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ac5dac1304634ad187f01e8c676ce9a3
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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