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    Piperonylic Acid - Black Pepper

    Uploaded by

    Sascha Koenen
    hansi

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    © All Rights Reserved
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    Piperonylic Acid - Black Pepper

    Uploaded by

    Sascha Koenen
    34 views2 pages
    hansi

    Original Title

    Piperonylic Acid.black Pepper

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    © © All Rights Reserved

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    TXT, PDF, TXT or read online from Scribd

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    hansi

    Copyright:

    © All Rights Reserved
    Download as TXT, PDF, TXT or read online from Scribd
    Download as txt, pdf, or txt
    34 views2 pages

    Piperonylic Acid - Black Pepper

    Uploaded by

    Sascha Koenen
    hansi

    Copyright:

    © All Rights Reserved
    Download as TXT, PDF, TXT or read online from Scribd
    Download as txt, pdf, or txt
    of 2

    Piperonylic acid from Black Pepper:

    ----------------------------------Preparation of Piperine
    One ounce (28 grams) of standard black pepper was placed in a 500 ml flat bottom
    flask along with 250ml Everclear to which a condenser was attached to prepare
    for standard reflux. With vigorous magnetic stirring, the mixture was refluxed
    at just above boiling temperature for 3 hours, allowed to cool, and the mixture
    was suction filtered to retrieve the filtrate. Standard distillation
    concentrated the filtrate to approximately 20 ml. The concentrated extract was
    then added to 20 ml of 10% KOH in Everclear which was heated on a low setting on
    a hot plate. To this mixture, water was added dropwise to form a yellow
    precipitate until no more precipitate formed. This was suction filtered and
    recrystallized with 30 ml of hardware-store acetone made anhydrous by drying
    with epsom salts. Yield was approximately 1.3g of crude piperine, which was
    stored in a dark place overnight. (approximate because the scale in question was
    at best accurate to tenths of grams.) You can do this a couple of times in a
    night without much effort, which can effectively yield 2.5 grams.
    Hydrolysis of Piperine to Piperic Acid and Piperidine
    2 grams of piperine was placed in 20 ml of a 10% KOH in Everclear solution in a
    125 ml Erlenmeyer flask and was refluxed using a standard reflux setup for 2
    hours. The original article recommends refluxing under reduced pressure, but
    there should not be a problem with standard reflux. It's your choice. There is
    no shortage of duct tape or chemical burns around these parts, so don't listen
    to the author.
    The solution was then transferred to a suitable vacuum distillation apparatus
    (a 100ml flask would be ideal) and the distillate was collected in an ice cooled
    receiving flask. The remaining undistilled residue was scraped out of the
    distillation flask and placed in 100 ml of H2O. The solution was acidified with
    HcL. The yellow precipitate was vacuum filtered and recrystallized with hot
    Everclear to yield approximately 1.5 grams of predominantly piperic acid, which
    was confirmed by a melting point of 213 degrees.
    Phase Transfer Oxidation Of Piperic Acid
    "In a 250 ml two- or three-necked round bottomed flask, place 1.0g of piperic
    acid, .1 g of Adogen 464, 10-15 ml of benzene, and a magnetic stirring bar.
    Attach a thermometer to the flask through a cork or adapter as well as a small
    dropping funnel. Add to this stirred mixture 4.4g of potassium permanganate
    dissolved in 50-60 ml of water at such a rate that the reaction temperature
    remains below 30 degrees. After all of the potassium permanganate has been
    added, stir at room temperature for 90 minutes. Finally, add about 10-20 ml of
    saturate sodium bisulfite solution to the reaction mixture and collect the
    preciptated manganese dioxide by suction filtration. Wash the precipitate with
    10 ml of benzene. Place the filtrate in a separatory funnel, separate the
    layers, and wash the benzene layer three times with 10ml of 10% NaOH solution.
    Wash the base solution once with 20ml of ether. Carefully acidify the base
    solution to pH 1-2 with 6M HcL and extract the acid solution with 3x25ml ether.
    Dry the ether solution over magnesium sulfate, filter, and then remove the ether
    by use of a rotary evaporator. The yield was approx. .3 grams piperonylic acid."
    Obviously, some sort of scale up is necessary to get an amount of product for a
    workable synth.
    Reference: Page 527 of _Laboratory Experiments In Organic Chemistry_
    by Mohrig and Neckers, no doubt long out of print.

    [http://www.rhodium.ws/chemistry/piperine.txt]

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