Descripción
4-Methoxyphenylacetic Acid CAS 104-01-8 Quick Details
| Nombre químico: | 4-Methoxyphenylacetic Acid |
| Otros nombres: | Homoanisic acid; Homo-p-anisic acid |
| CAS: | 104-01-8 |
| EINECS: | 203-166-4 |
| Tipo: | Pharmaceutical intermediates; Synthetic material intermediates; Organic raw materials |
| Fórmula molecular: | C9H10O3 |
| Peso molecular: | 166.17 |
4-Methoxyphenylacetic Acid CAS 104-01-8 Chemical Properties
| Punto de fusión | 84-86 °C(lit.) |
| Punto de ebullición | 140 °C3 mm Hg(lit.) |
| densidad | 1.1708 (rough estimate) |
| presión de vapor | 0.071Pa at 25℃ |
| índice de refracción | 1.5101 (estimate) |
| Fp | 193°C |
| temperatura de almacenamiento | Conservar por debajo de +30°C. |
| solubilidad | 6g/l |
| pka | pK1:4.358 (25°C) |
| formulario | Crystalline Powder and Chunks |
| color | White to light yellow |
| Solubilidad en agua | 6 g/L (20 ºC) |
| Punto de fusión | 84-86 °C(lit.) |
| Punto de ebullición | 140 °C3 mm Hg(lit.) |
What is 4-Methoxyphenylacetic Acid?
4-Methoxyphenylacetic acid, also known as p-methoxyphenylacetic acid, typically appears as white flaky crystals with a melting point of 84-86 °C. It dissolves quickly in hot water, ethyl acetate, ethanol, and ether, while being less soluble in cold water. This compound serves as an important intermediate in the synthesis of the antidepressant Venlafaxine, as well as various cardiovascular drugs, including puerarin and isoflavones.
The synthesis of 4-methoxyphenylacetic acid begins with p-methoxyacetophenone. In this process, ethanol, sulfur, and piperazine hexahydrate are added to a reaction pot and refluxed for four hours. Following this, the ethanol is distilled off. The resulting piperazine sulfide is then reacted with p-methoxyacetophenone at 135-140 °C for 20 hours. Afterward, sodium hydroxide is introduced, and the mixture is refluxed for another 20 hours. Once the reaction completes, the mixture is cooled to below 35 °C, and the pH is adjusted to 8-9 using hydrochloric acid. After centrifugation to remove sulfur, the solution is neutralized to a pH of 3-4, cooled again, centrifugally dehydrated, and the resulting crude product is refined to yield 4-methoxyphenylacetic acid.
Uses of 4-Methoxyphenylacetic Acid
4-Methoxyphenylacetic acid is found in microbial phenolic metabolites present in human feces after consuming beverages like gin and red wine. In the pharmaceutical industry, it plays a crucial role as an intermediate for synthesizing puerarin, which is used in treating cardiovascular diseases. Additionally, it has potential as a plasma biomarker for the early detection of non-small cell lung cancer.
This compound is also utilized in the manufacture of dextromethorphan, a common cough suppressant. Moreover, 4-methoxyphenylacetic acid can be used to:
- Prepare 4-methoxyphenylacetic acid methyl ester using mesoporous zirconia sulfate catalyst and dimethyl carbonate in esterification reactions.
- Serve as a ligand for synthesizing binuclear gallium (III) and phenyltin (IV) carboxylate metal complexes, which have significant pharmacological relevance.
- Act as a reactant in the Perkin reaction, enabling the synthesis of hydroxylated (E)-stilbene with substituted benzaldehyde.
Overall, 4-methoxyphenylacetic acid is a versatile compound with important applications in both organic synthesis and pharmaceutical development.
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