Ethyl benzoylacetate CAS 94-02-0 | 801808
CONSTITUTION: The alcohol dehydrogenase-producing microorganisms for the synthesis of optically active ethyl 3-hydroxy-3-phenylpropionate from ethyl benzoylacetate are Candida parapsilosis IFO 0708, Candida parapsilosis KCTC 7653, Geotrichum candidum IFO 4597, Kluyveromyces lactis KCTC 7133, Kluyveromyces marxianus KCTC 7524, Saccharomyces cerevisiae KCTC 1218, Saccharomyces cerevisiae KCTC 1552 and Saccharomyces cerevisiae KCTC 7917 and the optically active ethyl 3-hydroxy-3-phenylpropionate is (R)- and (S)-ethyl 3-hydroxy-3-phenylpropionate.
CAS 94-02-0, EC Number 202-295-3, chemical formula C₆H₅COCH₂COOC₂H₅
A new and facile synthesis of tolterodine using ethyl benzoylacetate as the starting material was developed. Reduction using sodium borohydride in methanol followed by Friedel–Crafts alkylation utilizing FeCl3·6H2O as catalyst lead to the known 2-(3-hydroxy-1-phenylpropyl)-4-methylphenol intermediate. Consecutive protection of phenolic OH with -toluenesulfonyl chloride via two-phase reaction and conversion of aliphatic OH using -nitrobenzenesulfonyl chloride facilitates direct substitution of diisopropylamine. After simultaneous deprotection of the tosyl group, optically pure ()-tolterodine·-tartrate was obtained by resolution using -tartaric acid with 99.99% purity.
Ethyl benzoylacetate is used as a flavoring agent and an intermediate in organic synthesis. Further, it is used in the preparation of triazipinones, iodonium ylides, ethyl 2-fluoro-2-benzolyacetate and benzo[c]furan-4,7-diones. It is involved in the Clisen condensation reaction with malononitrile to prepare 2-cyano-5-phenyl-3,5-dioxopentanonitrile.