Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phenol | HCID 996 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Fluoro-2-methyl-benzoic acid tert-butyl ester | HCID 89580571 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 89580837 | HCID 89580837 | 86% |
Reaction Steps
To a solution of tert-butyl 4-fluoro-2-methylbenzoate (1 g, 4.8 mmol) in methylsulfinylmethane (45 mL) were added phenol (0.43 g, 4.6 mmol) and potassium carbonate (1.24 g, 9 mmol). Then the mixture was stirred at 130° C. for 12 hours. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, washed with water (20 mL). The organic phase was separated and concentrated to give a residue. The residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give tert-butyl 2-methyl-4-phenoxybenzoate (1.1 g, 86%) as a yellow solid. LRMS (M+H+) m/z: calcd 284.14. found 284.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206128B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-7daf1a9f677f4196ba0ef5cd8048b3f3 |
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| Source note | uspto-grants-2015_12 |
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