Synthesis of Stilbene and Derivatives

Synthesis of Stilbene and Derivatives - Experiment Two...

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Experiment Two Synthesis of Stilbene and Derivatives Chemistry Department San Jose State University, San Jose, California, United State November, 13 th , 2011 Oxidation of an alcohol such as (-)-menthol using pyridinium chlorochromate(PCC) will reduce the alcohol and form ketone. This reaction is a modification of Jones oxidation reaction which originally would be done using chromic acid and sulfuric acid in acetone to reduce the alcohol. In this experiment, a cyclic compound (-)-menthol in (1R,2S,5R) configuration with a secondary alcohol was to reacted with PCC to reduce to a (-)-menthone. The cyclic ketone was allowed to react in acidic environment of glacial acetic acid and diluted hydrochloric acid. The reaction attempted to yield a different isomer of the compound, in this case identified as (+)-Isomenthone. Then (-)-Menthone was reduced in Sodium Borohydride in diluted Hydrochloric acid back to menthol and derivatives, in this reaction identified as neomenthone. Result and discussion Scheme 1: Reduction of menthol An equivalent amount of solid PCC 2 (4.859g, 22.5 mmol) and solid SiO 2 (4.852g, 80.72 mmol) were weighted and placed in a mortar to be grinded up and mixed thoroughly into an evenly orange compound. The solid mixture was transferred into a 250mL
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This note was uploaded on 04/03/2012 for the course CHEM 131A taught by Professor Nemes during the Winter '12 term at San Jose State University .

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Synthesis of Stilbene and Derivatives - Experiment Two...

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