Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Benzoylacetonitrile | HCID 64799 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 3525985 | HCID 3525985 | — |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150577B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-7f77df4e2f994d2c9d98ca73bd8c3592 |
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| Source note | uspto-grants-2015_10 |
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