Ethylene Glycol → HCID 11159613, compound

HRID 219894Notes

Reaction equation

HRID 219894 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:2].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1>[O:2]1[CH2:11][CH2:12][O:13][CH:1]1[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 90670m-Formylbenzonitrile

Product 1

HCID 11159613HCID 11159613, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-formyl-benzonitrile (2 g, 15.25 mmol, 1 eq) in dry toluene (30 mL), paratoluenesulfonic acid (262 mg, 1.5 mmol, 0.1 eq) and ethylene glycol (12.8 mL, 228 mmol, 15 eq) were added and the mixture was heated to reflux in a Dean-Stark apparatus overnight. The toluene was concentrated and the reaction mixture purified by flash chromatography (EtOAc/cHex) to afford the title compound as a colorless liquid (2000 mg, 74%). 1H NMR: (CDCl3, 300 MHz) δ 7.78 (m, 1H), 7.69 (m, 1H), 7.64 (m, 1H), 7.48 (t, J=7.7 Hz, 1H), 5.81 (s, 1H), 4.08 (m, 4H). HPLC (Method A) Rt: 2.45 min (purity: 92.1%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux in a Dean-Stark apparatus overnight
  3. concentrationThe toluene was concentrated
  4. customthe reaction mixture purified by flash chromatography (EtOAc/cHex)

Sources & evidence

ORD record
ord-ba8937973135466abcda6a234a34bb52
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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