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Volumn 11, Issue 3, 2007, Pages 422-430

Scale-Up Syntheses of Two Naturally Occurring Procyanidins: (-)-Epicatechin-(4β,8)-(+)-catechin and (-)-Epicatechin-3-0-galloyl- (4β, 8)-(-)-epicatechin-3-0-gallate

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EID: 39049136535     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700031n     Document Type: Article
Times cited : (39)

References (47)
  • 43
    • 39049100353 scopus 로고    scopus 로고
    • Dess-Martin periodinane (DMP) used in the process was purchased from commercial sources. The literature indicates that the intermediate [1-hydroxy-1, 2-benziodoxol-3(1H)-one] is explosive under excessive heating (>200 °C) or impact [J.B. Plumb & D.J. Harper, Chem. Eng. News 1990, July 16, 3, In our experience, the oxidation of the secondary alcohol was found to be slow when DMP was used in dry methylene chloride and required several hours for the completion of the reaction. However, when wet methylene chloride [S.D. Meyer & S.L. Schreiber, J. Org. Chem. 1994, 59, 7549] was used, the reaction required only 2 to 3 h for completion and a very mild exotherm was observed (∼5 to 8 °C) at the 440-g scale reaction. We have also observed that the rate of the addition of wet methylene chloride controls the exotherm and rate of the reaction
    • Dess-Martin periodinane (DMP) used in the process was purchased from commercial sources. The literature indicates that the intermediate [1-hydroxy-1, 2-benziodoxol-3(1H)-one] is explosive under excessive heating (>200 °C) or impact [J.B. Plumb & D.J. Harper, Chem. Eng. News 1990, July 16, 3]. In our experience, the oxidation of the secondary alcohol was found to be slow when DMP was used in dry methylene chloride and required several hours for the completion of the reaction. However, when wet methylene chloride [S.D. Meyer & S.L. Schreiber, J. Org. Chem. 1994, 59, 7549] was used, the reaction required only 2 to 3 h for completion and a very mild exotherm was observed (∼5 to 8 °C) at the 440-g scale reaction. We have also observed that the rate of the addition of wet methylene chloride controls the exotherm and rate of the reaction.
  • 44
    • 0043240879 scopus 로고    scopus 로고
    • and references cited therein
    • Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029 and references cited therein.
    • (2003) Chem. Rev , vol.103 , pp. 3029
    • Tang, W.1    Zhang, X.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.