HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | Methyl 4-hydroxy-2,5-dimethylbenzoate | HCID 22615980 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate | HCID 86605503 | 90.6% |
Reaction Steps
Trifluoromethanesulfonic anhydride (0.27 g) was added to an ice-cooled mixture of methyl 4-hydroxy-2,5-dimethylbenzoate (0.144 g) and pyridine (0.095 g) in methylene chloride (10 mL) with stirring. The mixture was stirred at room temperature for 30 min, and poured into a mixture of ethylacetate and 2 mol/L hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:n-hexane:ethyl acetate=10/1) to afford the title compound (0.226 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07423185B2 |
| Source dataset | uspto-grants-2008_09 |
| ORD ID | ord-1ca620ff2ff340b0a60419aa8d58879a |
| Source note | uspto-grants-2008_09 |