HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 2-(4-Hydroxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-(4-Methoxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester | HCID 90118224 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(4-Hydroxy-2,3-dimethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester | HCID 90118005 | 79.4% |
Reaction Steps
2-(4-Methoxy-2,3-dimethyl-phenyl)-cyclopropane carboxylic acid ethyl ester (0.32 g, 1.29 mmol) obtained in Step B was dissolved in DCM (5 mL), and the reactant was cooled to 0˜5° C. BBr3 solution (3.90 mL, 3.87 mmol, 1M/DCM) was added dropwise thereto, and the mixture was stirred at 0˜5° C. for 2 hours. After the termination of the reaction, EtOH and saturated sodium bicarbonate solution were added thereto in turn, and the mixture was stirred. The separated organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.24 g, 79%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447044B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-f14a97a08abe4d9d95ff15ad7ee75b70 |
| Source note | uspto-grants-2016_09 |