Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzoic anhydride | HCID 7167 | — |
| Reactant | Phenylacetonitrile | HCID 8794 | — |
| Reactant | 3,4,5-Trimethoxyphenol | HCID 69505 | — |
| Reactant | Sodium Benzoate | HCID 517055 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 11740970 | HCID 11740970 | — |
Reaction Steps
The title compound is prepared from heating a mixture of ω-phenyl-6-hydroxy-2,3,4-trimethoxy-acetophenone (0.996 g, 3.3 mmol), benzoic anhydride (6 g, 13.3 mmol) and sodium benzoate (6.5 g, 22.5 mmol) at 180-190° C. for 6 hr according to the published procedure (Wu, E S C et al. J. Med. Chem. 1988, 32, 183-192). Similar to the preparation ω-phenylresacetophenone (Wu, E S C et al. J. Med. Chem. 1987, 30, 788-792), ω-phenyl-6-hydroxy-2,3,4-trimethoxy-acetophenone is, in turn, obtained from adding anhydrous zinc chloride to a solution of 3,4,5-trimethoxyphenol and benzyl cyanide in ethyl acetate followed by bubbling HCl into the reaction mixture at room temperature and then heating at 95-100° C. with water.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08138165B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-8a5fcb56bec4460e8dd8ad2593dafc2c |
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| Source note | uspto-grants-2012_03 |
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