| Identification | More | [Name]
3-(3,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER | [CAS]
4687-37-0 | [Synonyms]
Ethyl veratroylacetate
ETHYL 3,4-DIMETHOXYBENZOYLACETATE
Ethyl 3,4-diMethoxybenzoylacetate 97%
Ethyl 3-oxo-3-(3,4-dimethoxyphenyl)propanoate
ETHYL 3-(3,4-DIMETHOXYPHENYL)-3-OXOPROPANOATE
Benzenepropanoicacid, 3,4-dimethoxy-b-oxo-, ethyl ester
Benzenepropanoic acid, 3,4-dimethoxy-β-oxo-, ethyl ester
3-(3,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER | [Molecular Formula]
C13H16O5 | [MDL Number]
MFCD03424826 | [Molecular Weight]
252.26 | [MOL File]
4687-37-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
37-41 °C (lit.) | [Boiling point ]
150-160 °C(Press: 0.01 Torr) | [density ]
1.136±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [pka]
10.77±0.48(Predicted) | [Appearance]
Colorless to light yellow <37°C Solid,>41°C Liquid | [CAS DataBase Reference]
4687-37-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
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| Hazard Information | Back Directory | [Synthesis]
GENERAL STEPS: The synthesis of ethyl 3,4-dimethoxybenzoylacetate from 3,4-dimethoxyacetophenone and diethyl carbonate was carried out as follows: first, 3,4-dimethoxyacetophenone (0.05 mol) was dissolved in toluene (50 mL) and then added slowly and dropwise to a solution containing diethyl carbonate (0.10 mol) and sodium hydride (0.15 mol, 60% mineral oil dispersion) (0.15 mol, 60% mineral oil dispersion). The reaction mixture was stirred at room temperature and heated to reflux for 30 minutes. Upon completion of the reaction, the mixture was poured into ice water, acidified with glacial acetic acid and subsequently extracted with ethyl acetate (3 x 100 mL). The organic phases were combined and dried with anhydrous magnesium sulfate. After removal of solvent by distillation under reduced pressure, the crude product was purified by silica gel column chromatography using dichloromethane as eluent to afford the target product ethyl 3,4-dimethoxybenzoylacetate. All the synthesized compounds were subjected to structural confirmation by 1H NMR, 13C NMR, IR and mass spectrometry. | [References]
[1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5064 - 5075
[2] Heterocycles, 1979, vol. 13, p. 239 - 246
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3217 - 3227
[4] Patent: JP2005/82549, 2005, A. Location in patent: Page/Page column 19-20
[5] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7304 - 7307 |
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