Ethylene Glycol → HCID 3525985, compound

HRID 1748315Notes

Reaction equation

HRID 1748315 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].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25]>C1(C)C=CC=CC=1>[C:6]1([C:2]2([CH2:3][C:4]#[N:5])[O:25][CH2:24][CH2:23][O:1]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 64799Benzoylacetonitrile

Product 1

HCID 3525985HCID 3525985, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-oxo-3-phenylpropanenitrile (10 g, 68.8 mmol) and PTSA (0.027 g, 1.37 mmol) in toluene (120 mL) is added ethylene glycol (120 mL, 2057 mmol). The mixture is heated at 150° C. for 14 h. The solvent is evaporated under reduced pressure and the residue is washed with 10% 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% 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-7f77df4e2f994d2c9d98ca73bd8c3592
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…