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  • Seminario 4

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    David Martin Muñoz
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    The document describes synthetic routes for preparing various difunctional compounds. It involves the reaction of benzaldehyde and other carbonyl compounds with nucleophiles and electrophiles to install functional groups such as nitro, hydroxyl, bromo, ethyl ester, and acetal groups at different positions on the carbonyl compounds. Reaction conditions include use of bases, acids, oxidizing agents and reductants at varying temperatures to synthesize a variety of multi-substituted products.

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    Seminario 4

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    The document describes synthetic routes for preparing various difunctional compounds. It involves the reaction of benzaldehyde and other carbonyl compounds with nucleophiles and electrophiles to install functional groups such as nitro, hydroxyl, bromo, ethyl ester, and acetal groups at different positions on the carbonyl compounds. Reaction conditions include use of bases, acids, oxidizing agents and reductants at varying temperatures to synthesize a variety of multi-substituted products.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    Download as pdf or txt
    32 views4 pages

    Seminario 4

    Uploaded by

    David Martin Muñoz
    The document describes synthetic routes for preparing various difunctional compounds. It involves the reaction of benzaldehyde and other carbonyl compounds with nucleophiles and electrophiles to install functional groups such as nitro, hydroxyl, bromo, ethyl ester, and acetal groups at different positions on the carbonyl compounds. Reaction conditions include use of bases, acids, oxidizing agents and reductants at varying temperatures to synthesize a variety of multi-substituted products.

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    of 4

    Soluciones Seminario n 4: Compuestos difuncionales

    1.1) Benzaldehido

    EtONa
    a)

    NO2 EtOH

    NO2 2) H O+
    3

    OH

    1) KOH, 100 C

    piridina

    H2O
    C
    CHO

    HS

    SH

    E
    S

    nBuLi

    H3C

    BF3

    H3C

    COOH

    2) H3O+

    OH

    b) H3C

    OH

    CrO3

    TiCl3

    NO2

    H3C

    H3C
    H3C

    1)

    CH3

    2) H3O+

    H3C

    c)

    H3C

    CH3

    CHO EtOH

    K
    d)

    CO2Et

    H3C

    CH3
    CH3

    CrO3 H3C
    piridina
    CH3

    OH

    CH3
    O

    I
    O
    O

    Hg2+
    H2O

    OH

    KCN (cat)
    O

    OH

    1) KOH,

    KMnO4

    2) H3O+

    OH

    O
    O

    COOH

    1) EtONa/EtOH
    2) H3O+
    N O

    e)

    1) EtONa/EtOH
    CO2Et 2) H3O+

    O O

    f)

    PBr3
    CO2H

    Br2

    OH

    Br
    COBr

    CH3

    CH3OH

    Br

    1) Zn
    COOCH3 2)

    3)

    H3C
    CHO

    H3O+

    CH3
    COOCH3

    g)
    NO2

    HNiPr

    h) Acetaldehdo

    SH

    BF 3

    H3C

    n-BuLi

    THF

    CH3

    THF

    NO2 S

    S
    U

    TiCl3

    CH3

    CHCl3
    60 C

    SH

    CH3

    H3C

    H3C
    V

    T
    O

    S
    H3C
    HO

    HO

    C6H5

    X
    O
    OEt

    i)

    CO2Et

    CO2Et

    CO2Et

    NaOEt/EtOH

    OEt
    O

    CH3

    [A]

    C6H5

    H3O+/

    O
    O

    CH3
    D

    j)

    CH 3

    2.CHO

    HS

    a)

    H 3C

    H 3C

    BF3

    Hg2+
    H2O

    H 3C

    CH 3

    b)

    CO 2Et

    1) NaOEt/EtOH

    2) 1/2 equiv
    Br

    Br

    1)

    CHO

    2) H3O+

    CrO3
    piridina
    O

    OH
    CO 2Et

    nBuLi

    SH

    (mayoritario)

    EtO 2C
    EtO 2C

    CO 2Et
    CO 2Et

    1) NaOEt/EtOH

    2) 1 equiv
    Br

    Br

    EtO 2C

    CO 2Et

    EtO 2C

    CO 2Et
    Br
    NaOEt/EtOH

    CO 2H
    HO 2C

    CO 2Et

    1) HO-

    2) H3O+, EtO 2C
    EtO 2C

    CO 2Et

    c)

    CO 2Et

    1) NaOEt/EtOH

    CO 2Et 2) Br2

    CO 2Et

    CO 2Et
    Br

    CO 2Et

    CO 2Et

    NH 2

    CO 2Et

    1) NaOEt/EtOH

    CO 2H

    CO 2Et

    2) Br-CH2-C6H5
    O

    CO 2Et
    CO 2Et

    1) NaOEt/EtOH

    2)

    OEt

    d)

    e)

    H3C

    2) H3O+,

    CHO

    1) NaOEt/EtOH

    2)

    2) 1/2 equiv Br2

    -CN

    H3C

    -O

    Ph

    CN

    H3C

    H3O+,

    CO2H
    OH

    OH

    Ph

    Ph

    HO

    2)

    H3O+,

    OEt

    O
    Ph

    1) HO-

    1) NaOEt/EtOH

    Br

    -OH

    OH

    3.- Ph

    CO 2H

    CO 2Et
    O

    1) HO-

    CO 2Et

    O
    Ph

    OH

    -OH

    Ph
    HO

    O
    Ph

    H 3O+

    Debe tratarse de carbonilos sin hidrgenos


    Ph
    HO

    HO
    HOOC

    CH 3
    CH 3

    H 3O+

    HO

    CH 3

    NC

    CH 3

    O-

    -CN

    H+

    CH 3
    CH 3

    O
    Ph

    OH

    4.-

    Ph-CHO

    CN- (cat)

    Ph

    Ph

    OH

    H 2O, EtOH

    O-

    O
    -CN

    H 2O

    C CN
    H

    OH

    OH

    C CN
    H

    C CN

    O
    H
    -OH

    O- OH
    C C
    CN H
    Ph

    Ph

    OH

    H 3C CH OH
    CN

    CH 3-CHO

    b)

    H 3C

    H 3C

    5.-

    OH OH
    C C
    CN H

    H 3C C

    H 3C

    CH 3

    H 3C
    O

    CH 3
    OH

    CO2Et

    CO2Et
    O

    2) H2O
    CO2Et

    OH

    OH
    CN

    1) Na OEt/ EtOH

    H3C

    OH OC C
    CN H

    H 2O

    H3C

    CO2Et H C
    3

    +
    C

    CH3

    EtO2C

    H3C
    H3C

    CH3
    O

    CO2Et

    D CH3

    H3C

    H3C
    CH3

    O
    H3C

    H3C

    CH3
    H3C

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