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    SYNTHESIS: A Solution of 20 G 3,4,5-Trimethoxybenzaldehyde, 40

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    Smoke
    A solution of 3,4,5-trimethoxybenzaldehyde, nitromethane, and cyclohexylamine was heated to produce beta-nitro-3,4,5-trimethoxystyrene. This was then reduced using lithium aluminum hydride to produce 3,4,5-trimethoxyphenethylamine hydrochloride. The compound was purified by distillation and crystallization to obtain white crystals. An alternate synthesis using 3,4,5-trimethoxyphenylacetonitrile is also described.

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    SYNTHESIS: A Solution of 20 G 3,4,5-Trimethoxybenzaldehyde, 40

    Uploaded by

    Smoke
    36 views1 page
    A solution of 3,4,5-trimethoxybenzaldehyde, nitromethane, and cyclohexylamine was heated to produce beta-nitro-3,4,5-trimethoxystyrene. This was then reduced using lithium aluminum hydride to produce 3,4,5-trimethoxyphenethylamine hydrochloride. The compound was purified by distillation and crystallization to obtain white crystals. An alternate synthesis using 3,4,5-trimethoxyphenylacetonitrile is also described.

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    Synthesis

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    A solution of 3,4,5-trimethoxybenzaldehyde, nitromethane, and cyclohexylamine was heated to produce beta-nitro-3,4,5-trimethoxystyrene. This was then reduced using lithium aluminum hydride to produce 3,4,5-trimethoxyphenethylamine hydrochloride. The compound was purified by distillation and crystallization to obtain white crystals. An alternate synthesis using 3,4,5-trimethoxyphenylacetonitrile is also described.

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    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    36 views1 page

    SYNTHESIS: A Solution of 20 G 3,4,5-Trimethoxybenzaldehyde, 40

    Uploaded by

    Smoke
    A solution of 3,4,5-trimethoxybenzaldehyde, nitromethane, and cyclohexylamine was heated to produce beta-nitro-3,4,5-trimethoxystyrene. This was then reduced using lithium aluminum hydride to produce 3,4,5-trimethoxyphenethylamine hydrochloride. The compound was purified by distillation and crystallization to obtain white crystals. An alternate synthesis using 3,4,5-trimethoxyphenylacetonitrile is also described.

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    of 1

    SYNTHESIS: A solution of 20 g 3,4,5-trimethoxybenzaldehyde, 40

    mL nitromethane, and 20 mL cyclohexylamine in 200 mL of acetic


    acid was heated on the steam bath for 1 h. The reaction mixture was
    then diluted slowly and with good stirring, with 400 mL H2O, which
    allowed the formation of a heavy yellow crystalline mass. This was
    removed by filtration, washed with H2O, and sucked as dry as
    possible. Recrystallization from boiling MeOH (15 mL/g) yielded, after
    filtration and air drying, beta-nitro-3,4,5-trimethoxystyrene as bright
    yellow crystals weighing 18.5 g. An alternate synthesis was effective,
    using an excess of nitromethane as solvent as well as reagent, if the
    amount of ammonium acetate catalysis was kept small. A solution of
    20 g 3,4,5-trimethoxybenzaldehyde in 40 mL nitromethane
    containing 1 g anhydrous ammonium acetate was heated on the
    steam bath for 4 h. The solvent was stripped under vacuum and the
    residual yellow oil was dissolved in two volumes of hot MeOH,
    decanted from some insolubles, and allowed to cool. The crystals
    formed are removed by filtration, washed with MeOH and air dried
    yielding 14.2 g. of bright yellow crystals of beta-nitro-3,4,5-
    trimethoxystyrene. The use of these proportions but with 3.5 g
    ammonium acetate gave extensive side-reaction products even when
    worked up after only 1.5 h heating. The yield of nitrostyrene was, in
    this latter case, unsatisfactory.

    To a gently refluxing suspension of 2 g LAH in 200 mL Et2O, there


    was added 2.4 g beta-nitro-3,4,5-trimethoxystyrene as a saturated
    Et2O solution by use of a Soxhlet extraction condenser modified to
    allow the continuous return of condensed solvent through the
    thimble. After the addition was complete, the refluxing conditions
    were maintained for another 48 h. After cooling the reaction mixture,
    a total of 150 mL of 1.5 N H2SO4 was cautiously added, destroying
    the excess hydride and ultimately providing two clear phases. These
    were separated, and the aqueous phase was washed once with 50 mL
    Et2O. There was then added 50 g potassium sodium tartrate,
    followed by sufficient NaOH to bring the pH >9. This was then
    extracted with 3x75 mL CH2Cl2, and the solvent from the pooled
    extracts was removed under vacuum. The residue was distilled at
    120-130 °C at 0.3 mm/Hg giving a white oil that was dissolved in 10
    mL IPA and neutralized with concentrated HCl. The white crystals that
    formed were diluted with 25 mL Et2O, removed by filtration, and air
    dried to provide 2.1 g 3,4,5-trimethoxyphenethylamine hydrochloride
    (M) as glistening white crystals. The sulfate salt formed spectacular
    crystals from water, but had a broad and uncharacteristic mp. An
    alternate synthesis can employ 3,4,5-trimethoxyphenylacetonitrile, as
    described under beta-D.

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