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| | ACETONYLMALONIC ACID DIETHYL ESTER Basic information |
| Product Name: | ACETONYLMALONIC ACID DIETHYL ESTER | | Synonyms: | DIETHYL ACETONYLMALONATE;DIETHYL 2-OXOPROPYLMALONATE;ACETONYLMALONIC ACID DIETHYL ESTER;2-OXOPROPYLMALONIC ACID DIETHYL ESTER;3-Oxobutane-1,1-dicarboxylic acid diethyl ester;2-Oxopropylmalonic acid eiethyl ester;ACETONYLMALONIC ACID DIETHYL ESTER or diethyl 2-(2-oxopropyl)malonate;1,3-diethyl 2-(2-oxopropyl)propanedioate | | CAS: | 23193-18-2 | | MF: | C10H16O5 | | MW: | 216.23 | | EINECS: | | | Product Categories: | | | Mol File: | 23193-18-2.mol |  |
| | ACETONYLMALONIC ACID DIETHYL ESTER Chemical Properties |
| Boiling point | 296.4±20.0℃ (760 Torr) | | density | 1.091±0.06 g/cm3 (20 ºC 760 Torr) | | refractive index | 1.4388 (20℃) | | Fp | 126.9±21.8℃ | | storage temp. | 2-8°C | | form | clear liquid | | pka | 11.80±0.59(Predicted) | | color | Colorless to Light yellow |
| | ACETONYLMALONIC ACID DIETHYL ESTER Usage And Synthesis |
| Uses | Diethyl Acetonylmalonate is a doubly functionalized reagent, the ketone acting as an internal trapping agent after the reaction of the malonate anion; for synthesis of five-membered rings.
| | Synthesis Reference(s) | The Journal of Organic Chemistry, 46, p. 4631, 1981 DOI: 10.1021/jo00335a084 | | Synthesis |
A detailed procedure reports the alkylation of Diethyl Malonate by chloroacetone on a 100 g scale, giving diethyl acetonylmalonate (1) with a yield of 55% after distillation. Since chloroacetone is toxic and highly irritating to the eyes, skin, and mucous membranes, an alternative procedure using Isopropenyl Acetate, a mild irritant and a much less toxic compound than chloroacetone, should be seriously considered. Thus the reaction of dimethyl malonate with isopropenyl acetate in the presence of Cerium(IV) Ammonium Nitrate (CAN) followed by a mild basic treatment affords dimethyl acetonylmalonate in a yield of 82% on a 5-10 g scale (eq 1). This procedure offers advantages regarding the yield and reaction conditions, and it uses available starting materials.
| | References |
1. Mercier C.; Addas A. R.; Deslongchamps P. CJC 1972, 50, 1882.
2. The Merck Index, 11th ed.; Merck: Rahway, NJ, 1989.
3. Baciocchi E.; Civitarese G.; Ruzziconi R. TL 1987, 28, 5357.
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| | ACETONYLMALONIC ACID DIETHYL ESTER Preparation Products And Raw materials |
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