Ethylene Glycol → HCID 3525985, compound

HRID 1521745Notes

Reaction equation

HRID 1521745 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[CH2:12](O)[CH2:13][OH:14]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[C:6]1([C:2]2([CH2:3][C:4]#[N:5])[O:14][CH2:13][CH2:12][O:1]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 64799Benzoylacetonitrile

Product 1

HCID 3525985HCID 3525985, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-oxo-3-phenylpropanenitrile (10 g, 69 mmol) and PTSA (27 mg, 1.37 mmol) in toluene (120 mL) is added ethylene glycol (120 mL, 2057 mmol). The azeotropic mixture is heated at 150° C. for 14 h. The solvent is evaporated under reduced pressure and the residue is washed with 10% aqueous NaOH solution. The aqueous layer is extracted with diethyl ether (2×100 mL) and the combined organic layers are dried (Na2SO4) and evaporated to provide the crude compound. The crude material is purified over neutral alumina eluting with 1% of ethyl acetate/hexane to afford the title compound as an off-white solid (10 g, 77%).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washthe residue is washed with 10% aqueous NaOH solution
  3. extractionThe aqueous layer is extracted with diethyl ether (2×100 mL)
  4. dry with materialthe combined organic layers are dried (Na2SO4)
  5. customevaporated
  6. customto provide the crude compound
  7. customThe crude material is purified over neutral alumina eluting with 1% of ethyl acetate/hexane

Sources & evidence

ORD record
ord-2121c895708f495f932c6351e5b1841d
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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