Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Fluoro-5-formylbenzonitrile | HCID 2769582 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 55255896 | HCID 55255896 | — |
Reaction Steps
To a solution of 2-fluoro-5-formylbenzonitrile (450 mg, 3 mmol) in toluene (10 mL) was added ethylene glycol (2 mL) and p-toluene sulfonic acid (25 mg). The solution was heated to 70° C. overnight. The solution was cooled to room temperature. Ethyl acetate (100 mL) was added and the solution was washed with sat. sodium bicarbonated (10 mL), water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated to a clear oil (567 mg, 98%). 1H NMR (400 MHz, CDCl3) δ 7.78 (dd 1H, J=6.3, 2.3 Hz), 7.74-7.70 (m, 1H), 7.27-7.24 (m, 1H), 5.80 (s, 1H), 4.14-4.08 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765748B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-cf1eca08b081485ca3750ba4e0a5211b |
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| Source note | uspto-grants-2014_07 |
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