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    Preparation of Aspirin From Salicylic Acid

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    Moona Sonika
    The document summarizes the preparation of aspirin from salicylic acid. Salicylic acid is reacted with acetic anhydride in the presence of sulfuric acid as a catalyst. This esterification reaction replaces the phenolic OH group of salicylic acid with an acetyl group, forming aspirin. Specifically, the procedure involves heating a mixture of salicylic acid, acetic anhydride and sulfuric acid on a water bath, then pouring the reaction into cold water. The crude aspirin product is recrystallized from ethanol and water to obtain purified aspirin. The percentage yield of the reaction can be calculated by comparing the practical and theoretical yields based on the molecular weights and amounts of reactants used.

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    Preparation of Aspirin From Salicylic Acid

    Uploaded by

    Moona Sonika
    217 views10 pages
    The document summarizes the preparation of aspirin from salicylic acid. Salicylic acid is reacted with acetic anhydride in the presence of sulfuric acid as a catalyst. This esterification reaction replaces the phenolic OH group of salicylic acid with an acetyl group, forming aspirin. Specifically, the procedure involves heating a mixture of salicylic acid, acetic anhydride and sulfuric acid on a water bath, then pouring the reaction into cold water. The crude aspirin product is recrystallized from ethanol and water to obtain purified aspirin. The percentage yield of the reaction can be calculated by comparing the practical and theoretical yields based on the molecular weights and amounts of reactants used.

    Original Title

    aspirin synthesis

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    The document summarizes the preparation of aspirin from salicylic acid. Salicylic acid is reacted with acetic anhydride in the presence of sulfuric acid as a catalyst. This esterification reaction replaces the phenolic OH group of salicylic acid with an acetyl group, forming aspirin. Specifically, the procedure involves heating a mixture of salicylic acid, acetic anhydride and sulfuric acid on a water bath, then pouring the reaction into cold water. The crude aspirin product is recrystallized from ethanol and water to obtain purified aspirin. The percentage yield of the reaction can be calculated by comparing the practical and theoretical yields based on the molecular weights and amounts of reactants used.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    217 views10 pages

    Preparation of Aspirin From Salicylic Acid

    Uploaded by

    Moona Sonika
    The document summarizes the preparation of aspirin from salicylic acid. Salicylic acid is reacted with acetic anhydride in the presence of sulfuric acid as a catalyst. This esterification reaction replaces the phenolic OH group of salicylic acid with an acetyl group, forming aspirin. Specifically, the procedure involves heating a mixture of salicylic acid, acetic anhydride and sulfuric acid on a water bath, then pouring the reaction into cold water. The crude aspirin product is recrystallized from ethanol and water to obtain purified aspirin. The percentage yield of the reaction can be calculated by comparing the practical and theoretical yields based on the molecular weights and amounts of reactants used.

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    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
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    Preparation of Aspirin from Salicylic acid

    Mrs Chanda Ranjan


    Department of Pharmaceutical Chemistry
    The Oxford College of Pharmacy, Bangalore
    Learning outcome

    1. How Aspirin is synthesized in the laboratory?

    2. Calculation of the practical yield.


    Content:

    • Materials Required.
    • Principle
    • Procedure
    • Calculation
    • Report.
    Materials Required

    Chemicals Required: Salicylic acid, acetic anhydride, conc Sulphuric acid, Ethanol.

    Apparatus Required: Beaker, Funnel, Stirrer, Pipette

    COOH
    1. Salicylic acid contains a phenol group, and phenols are known to be irritating.
    OH

    2. Due to this the phenol group was replaced with acetyl group that become
    (acetylsalicylic acid, also known as aspirin) which was shown to be much less
    Salicylic acid irritating than salicylic acid.

    COOH

    OCOCH3
    1. Chemically Aspirin is 2-Acetoxybenzoic acid.

    2. Aspirin is an effective analgesic (pain reliever), antipyretic (fever reducer) and


    Aspirin
    anti-inflammatory agent and is one of the most widely used non-prescription drugs.
    Acetyl salicylic acid

    Preparation of Aspirin from Salicylic acid


    Principle COOH
    COOH

    OCOCH3
    OH H2SO4
    (CH3CO)2O CH3COOH

    Acetic Acid
    Acetic Aspirin
    Salicylic acid
    anhydride Acetyl salicylic acid

    Reaction scheme for the synthesis of Aspirin

    1. Aspirin can be made by reacting salicylic acid with Acetic anhydride in the presence of an acid
    catalyst. This reaction is an example of Esterification reaction.
    2. The OH group (phenol group) on the salicylic acid forms an acetylated product with the acetic
    anhydride.
    3. Salicylic reacts with acetic anhydride and with the aid of acidic condition the acetate ion detaches

    from the acetic anhydride and gets attached to the hydrogen ion released from the phenolic OH
    4. group
    The and forms
    Acetic Acetic as
    acid formed acid
    theasbyproduct
    the byproduct.
    is washed with water and the remaining acetic anhydride
    also reacts with water to form acetic acid and then washed with water
    (CH3CO)2O H2O CH3COOH
    Acetic anhydride Acetic Acid
    5. And the hydrogen ion of phenolic OH is replaced with Acetyl group resulting the formation of Aspirin

    Preparation of Aspirin from Salicylic acid


    Procedure
    1. 10 gm of salicylic acid, 14 ml of acetic anhydride, and 2 ml of concentrated sulphuric acid was taken
    in a beaker and heated over the water bath for half an hour at 60 to 65 degree C with continuous stirring
    2. After heating the mixture was poured into the cold water with occasional stirring.

    10 gm Salicylic acid
    2ml conc Sulphuric acid
    14 ml acetic anhydride

    Water bath

    Preparation of Aspirin from Salicylic acid Cold Water


    Procedure
    3. After some time the crude Aspirin was filtered.
    4. The product will be dissolved in alcohol for recrystallization
    5. After that it will be poured into warm water so that the solid separates

    30 ml Ethanol + Crude Aspirin


    Warm
    water

    Crude aspirin Preparation of Aspirin from Salicylic acid


    Preparation of Aspirin from Salicylic acid
    6. The separated solid will be filtered and dried and after that its weight and melting point
    determination will be done.

    Aspirin
    White,
    Crystalline Solid
    melting point - 136 °C
    Cold Water boiling point - 140 °C .
    Preparation of Aspirin from Salicylic acid

    Calculation
    • Molecular weight of Salicylic acid = 138 gm
    • Molecular weight of Aspirin= 180 gm

    • 138 gm of salicylic acid gives  180 gm of Aspirin


    • Therefore, 10 gm of salicylic acid will give  180 x 10 = 13.04 gm of Aspirin
    ________ 138
    • Theoretical yield = 13.04 gm
    • Practical yield= ________ gm
    • Percentage yield= Practical Yield x 100
    ___________________
    Theoretical yield
    Thank You

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