Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Chloro-N,N-diethylacetamide | HCID 16844 | — |
| Reactant | Propyl 4-hydroxy-3-methoxyphenylacetate | HCID 104310 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | Propanidid | HCID 15004 | 95% |
Reaction Steps
3-Methoxy-4-hydroxyphenylacetic acid propyl ester (15-A) was dissolved in acetone. To the solution, 2 equivalents of K2CO3 were added, followed by 1.2 equivalent of 2-chloro-N,N-diethylacetamide. Under vigorous stirring, the suspension was warmed to reflux (60° C.) for ˜15 hours. After cooling to room temperature the reaction mixture was filtered and the remaining solvent removed under reduced pressure, giving a 95% yield of a dark yellow oil. The oily product was purified by silica column chromatography to produce the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06887866B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-26a08a0a2db1494991c5a525adbb8539 |
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| Source note | uspto-grants-2005_05 |
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