Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Bromomethyl)benzonitrile | HCID 86996 | — |
| Reactant | Methyl 3-Hydroxybenzoate | HCID 88068 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 7671523 | HCID 7671523 | 60% |
Reaction Steps
A mixture of 4-cyanobenzyl bromide (40 mmol, 7.84 g), methyl 3-hydroxybenzoate (40 mmol, 6.08 g) and potassium carbonate (60 mmol, 8.29 g) in 50 mL DMF was stirred at 60° C. overnight and the solution was cooled to room temperature. To it was added dilute citric acid followed by ethyl acetate. The organic layer was separated, washed with brine, NaHCO3 and brine, dried (MgSO4), and concentrated to give a solid. The solid was washed with ether two times to give 6.2 g (60%) product. NMR (DMSO-d6): δ7.88 (d,2H);7.66(d,2H);7.58 (m, 2H); 7.46 (t, 1H); 7.32 (dd, 1H); 5.30 (s, 2H); 3.84 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05691329 |
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| Source dataset | uspto-grants-1997_11 |
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| ORD ID | ord-e1e4fae377404c319b1b84c8125cf421 |
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| Source note | uspto-grants-1997_11 |
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