Rosenmund Reduction

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D. P. Wagner - One of the best experts on this subject based on the ideXlab platform.

Albert Israel Rachlin - One of the best experts on this subject based on the ideXlab platform.

Harvey Gurien - One of the best experts on this subject based on the ideXlab platform.

Erich Mosettig - One of the best experts on this subject based on the ideXlab platform.

  • the Rosenmund Reduction of acid chlorides to aldehydes
    Organic Reactions, 2011
    Co-Authors: Erich Mosettig, Ralph Mozingo
    Abstract:

    In the synthesis of complex molecules, particularly in connection with natural products, it is occasionally desirable to prepare an aldehyde when the readily available starting material is the corresponding acid. The Rosenmund Reduction is probably the most useful method for application to a large number of aldehdyes of varied types. The Rosenmund Reduction consists in the selective hydrogenation of an acid chloride in the presence of a suitable catalyst, usually supported palladium to the corresponding aldehyde. Keywords: Rosenmund Reduction; acid chlorides; aldehydes; catalyst; regulator; solvent; hydrogen; precautions; experimental procedures

  • Organic Reactions - The Rosenmund Reduction of Acid Chlorides to Aldehydes
    Organic Reactions, 2011
    Co-Authors: Erich Mosettig, Ralph Mozingo
    Abstract:

    In the synthesis of complex molecules, particularly in connection with natural products, it is occasionally desirable to prepare an aldehyde when the readily available starting material is the corresponding acid. The Rosenmund Reduction is probably the most useful method for application to a large number of aldehdyes of varied types. The Rosenmund Reduction consists in the selective hydrogenation of an acid chloride in the presence of a suitable catalyst, usually supported palladium to the corresponding aldehyde. Keywords: Rosenmund Reduction; acid chlorides; aldehydes; catalyst; regulator; solvent; hydrogen; precautions; experimental procedures

  • Organic Reactions - The Synthesis of Aldehydes from Carboxylic Acids
    Organic Reactions, 2011
    Co-Authors: Erich Mosettig
    Abstract:

    The Rosenmund Reduction of acid chlorides to the corresponding aldehydes was discussed in volume 4 of this series. There are a number of other less direct methods by which carboxylic acids can be converted into aldehydes and the purpose of this chapter is to consider the more useful of these procedures. Three of these methods, the hydrolytic decomposition of Reissert's compounds, the method of Grundmann, and the reductive desulfurization of thiol esters require acid chlorides as intermediates and in the respect are competitive with the Rosenmund Reduction of acid chlorides. In the fourth method method, the McFadyen and Stevens synthesis, acid chlorides may be used for the preparation of the intermediate acyl hydrazides. Two additional methods, (Sonn and Muller, and Stephen) are based on the intermediate imido chlorides. These methods listed appear to be the one ones developed to the point where further discussion is profitable. Keywords: aldehydes; carboxylic acids; Reissert's compounds; Grundman method; reductive desulfurization; thio esters; McFadyen and Stevens method; Sonn and Muller method; Stephen method; nitriles; controlled Reduction; amides; lithium aluminum hydride

Michael Urquhart - One of the best experts on this subject based on the ideXlab platform.

  • Discovery and Development of an Efficient Process to Atovaquone
    Organic Process Research & Development, 2012
    Co-Authors: Hugh Britton, David Catterick, Andrew Neil Dwyer, Andrew H. Gordon, Chris Mccormick, Clive E. Mountain, Alec Simpson, Stuart G. Leach, David R. Stevens, Michael Urquhart
    Abstract:

    The discovery and development of an efficient and more sustainable manufacturing route to the anti-pneumocystic agent atovaquone (2-((1R,4R)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione) 1 is described. The existing commercial route to atovaquone delivers a poor yield of product and uses expensive reagents. The new synthesis commences with readily available phthalic anhydride, which is converted to 1,4-isochromandione 5 and then to atovaquone 1 by reaction with 4-(4-chlorophenyl)cyclohexanecarboxylic acid 3 using key bromination, Rosenmund Reduction, and rearrangement chemistries. Downstream processing to atovaquone is both high yielding and robust, and the resulting process has been demonstrated on 200-kg scale. The process is simple, uses cheap raw materials, and is more sustainable in that it avoids low-yielding silver-promoted chemistry and isomerisation procedures. It includes a robust, facile, and highly efficient procedure to 1,4-isochromandione 5, and routes to 4-(4-chlorophenyl)cy...