Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Fluorobenzaldehyde | HCID 68023 | — |
| Reactant | Methyl 3-(benzyloxy)-5-hydroxybenzoate | HCID 7472028 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86666550 | HCID 86666550 | 96.5% |
Reaction Steps
To a single necked round bottomed flask fitted with stop cock with N2(g) balloon, in DMF was added Methyl 3-(benzyloxy)-5-hydroxybenzoate (24 g) (Intermediate 12). Under stirring, potassium carbonate (38 g) followed by 4-fluorobenzaldehyde (13.84 g) were added at room temperature. The reaction was heated at 90° C. for 16 h with constant stirring. The reaction mixture was diluted with water and extracted with EtOAc. All organic layers were combined and washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get crude thick liquid product. The crude product was purified by flash column chromatography to yield title compound (32.5 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08835469B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-67941696561f4572973b640745d35d6a |
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| Source note | uspto-grants-2014_09 |
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