Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Methyl Benzoate | HCID 7150 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Benzoylacetonitrile | HCID 64799 | — |
Reaction Steps
To a solution of benzoic acid methyl ester (1.0 equiv.) and methyl cyanide (2.0 equiv.) in anhydrous THF (1.0 M) was added sodium hydride (60% in mineral oil, 2 equiv.) under nitrogen. After the resulting reaction mixture was stirred at 70° C. overnight, the reaction mixture was quenched with ice-water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum afforded the crude product as a brown solid. 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.94-7.92 (m, 2H), 7.69-7.65 (m, 1H), 7.55-7.54 (m, 2H), 4.08 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156798B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-d2165186a844462daa2789132d2cc53b |
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| Source note | uspto-grants-2015_10 |
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