Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 2-Amino-1-(furan-2-yl)ethan-1-one--hydrogen chloride (1/1) | HCID 13226138 | — |
| Reactant | N-[2-(Furan-2-yl)-2-oxoethyl]acetamide | HCID 13773126 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67933391 | HCID 67933391 | — |
Reaction Steps
U.S. Patent 2,547,712 describes a process for producing certain 1-[2-furyl]-2-aminopropane diols. In a more relevant disclosure, in Example 2 of the '712 patent, the compound 2-furyl aminomethyl ketone hydrochloride is produced by reacting a 2-furyl bromomethyl ketone hexamethylene tetraamine complex with HCl. In the next step the 2-furyl aminomethyl ketone is added to a mixture of glacial acetic acid and acetic anhydride to which is then added sodium acetate. The product of that reaction is 2-furyl acetamidomethyl ketone, which is reacted with formalin, sodium bicarbonate and methanol to form 2-furyl-α-acetamido-β-hydroxyethyl ketone. This product was then reduced to the corresponding diol with aluminum isopropoxide (the catalyst of the '913 patent) in isopropanol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04962212 |
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| Source dataset | uspto-grants-1990_10 |
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| ORD ID | ord-d111ea77243242aeae3ec463bdb8dd68 |
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| Source note | uspto-grants-1990_10 |
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