Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzyl Chloride | HCID 7503 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 94283-73-5 | HCID 15453521 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11140186 | HCID 11140186 | 94% |
Reaction Steps
Potassium carbonate (1.83 g, 13.2 mmol) and benzyl chloride (1.55 mL, 13.5 mmol) were added to a suspension of 3-hydroxy-4-isopropoxybenzaldehyde described in Production Example 171 (1.84 g, 10.2 mmol) in ethanol (20 mL) under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 90° C. for 2 hours. The mixture was cooled to 0° C. and then 2 M hydrochloric acid, ethyl acetate, and water were added for partition. The organic layer was washed with a saturated saline solution, and the resultant was dried over anhydrous sodium sulfate, and then filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-3:1). The target fraction was concentrated under vacuum to obtain the title compound (2.59 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933099B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-3a5929b97bc8480e915d9f4df9009a08 |
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| Source note | uspto-grants-2015_01 |
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