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| | ETHYL 4-METHOXYBENZOYLACETATE Basic information |
| Product Name: | ETHYL 4-METHOXYBENZOYLACETATE | | Synonyms: | 3-keto-3-(4-methoxyphenyl)propionic acid ethyl ester;p-Anisoylacetic Acid Ethyl Ester
Ethyl p-Anisoylacetate
4-Methoxybenzoylacetic Acid Ethyl Ester;3-(4-Methoxy-phenyl)-3-oxo-propionic acid ethyl ester;2-(p-Methoxybenzoyl)acetic acid ethyl ester;3-(4-methoxyphenyl)-3-oxopropanoic acid ethyl ester;Acetic acid, p-anisoyl-, ethyl ester;P-ANISOYLACETIC ACID ETHYL ESTER;MOBEE | | CAS: | 2881-83-6 | | MF: | C12H14O4 | | MW: | 222.24 | | EINECS: | 220-733-1 | | Product Categories: | Pharmaceutical Intermediates;Benzoic acid | | Mol File: | 2881-83-6.mol |  |
| | ETHYL 4-METHOXYBENZOYLACETATE Chemical Properties |
| Boiling point | 154 °C1 hPa(lit.) | | density | 1.160 g/mL at 20 °C(lit.) | | refractive index | 1.5410 to 1.5460 | | Fp | 115°C | | storage temp. | Sealed in dry,Room Temperature | | solubility | H2O: soluble | | pka | 10.34±0.25(Predicted) | | form | clear liquid | | color | Light yellow to Yellow to Orange | | InChI | InChI=1S/C12H14O4/c1-3-16-12(14)8-11(13)9-4-6-10(15-2)7-5-9/h4-7H,3,8H2,1-2H3 | | InChIKey | KRAHENMBSVAAHD-UHFFFAOYSA-N | | SMILES | C1(=CC=C(OC)C=C1)C(=O)CC(=O)OCC | | CAS DataBase Reference | 2881-83-6(CAS DataBase Reference) | | EPA Substance Registry System | Benzenepropanoic acid, 4-methoxy-.beta.-oxo-, ethyl ester (2881-83-6) |
| Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 2918.99.4700 |
| | ETHYL 4-METHOXYBENZOYLACETATE Usage And Synthesis |
| Synthesis Reference(s) | Tetrahedron Letters, 14, p. 4207, 1973 DOI: 10.1016/S0040-4039(01)87150-1
Synthesis, p. 290, 1993 DOI: 10.1055/s-1993-25849 | | Synthesis | To a stirred mixture of sodium hydride (3 mol eq.) and diethyl carbonate (4 mol eq.) in 50 mL of tetrahydrofuran (THF) washed with hexane (3 x 15 mL), p-methoxyacetophenone (1 mol eq.) was slowly added dropwise for a controlled period of 30 min or more. The reaction mixture was heated and refluxed for 3-4 h until the color of the reaction solution changed to dark brown and the reaction progress was monitored by thin layer chromatography (TLC, unfolding agent 10% ethyl acetate/hexane). Upon completion of the reaction, the mixture was cooled to room temperature and acidified with 5 mL of glacial acetic acid, followed by the addition of 100 mL of ice-cold dilute hydrochloric acid solution. The aqueous phase was extracted with ethyl acetate (3 x 75 mL) and the organic phases were combined and washed sequentially with saturated sodium bicarbonate solution, saturated saline and deionized water. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give ethyl 3-(4-methoxyphenyl)-3-oxopropanoate as a viscous substance in good yield. The structure of the product was confirmed by 1H NMR and 13C NMR spectroscopy and the data were in agreement with literature reports. | | References | [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 31, p. 4543 - 4547
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4237 - 4244
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 34, p. 8661 - 8664
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5064 - 5075
[5] European Journal of Organic Chemistry, 2012, # 35, p. 6976 - 6985 |
| | ETHYL 4-METHOXYBENZOYLACETATE Preparation Products And Raw materials |
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