Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | (-)-Licarin A | HCID 6442393 | — |
| Solvent | Potassium Hydroxide | HCID 14797 | — |
| Product | HCID 86738149 | HCID 86738149 | — |
Reaction Steps
In a nitrogen atmosphere 10 g trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran are dissolved in 400 ml 2 N potash lye and treated with 37 ml 35 percent formalin solution, then held for 24 hours at 74° C. and treated twice within this period with the same amount of formaline solution. After cooling follows acidification with dilute hydrochloric acid until a pH of 1 is attained, then extraction with ether, washing of the ether phase with water, 5 percent NaHCO3 solution and water, and drying over Na2SO4. The oil remaining upon removal of the ether is crystallized from methylenechloride/petroleum ether (boiling point 60°-80° C.) and yields 7 g 5-[trans-2,3-dihydro-7-methoxy-3-methyl-5-(E)-propenylbenzofuran-2-yl]-2-hydroxy-3-methoxybenzyl alcohol, melting point 117°-119° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04304785 |
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| Source dataset | uspto-grants-1981_12 |
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| ORD ID | ord-3ca3167b96b149a0b4482bfbf79198fb |
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| Source note | uspto-grants-1981_12 |
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