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DraconicAcid
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Arecoline is an ester- a strong base like sodium hydroxide could hydrolyze it to the sodium salt of arecaidine. Try extracting the arecoline with a
solvent that's immiscible with water (arecoline is soluble in chloroform; that might work). The only trouble is that arecoline is very water-soluble,
so you'd need a lot of salt in the water to drive it into the organic phase.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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metalayer
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Quote: Originally posted by DraconicAcid  | | Arecoline is an ester- a strong base like sodium hydroxide could hydrolyze it to the sodium salt of arecaidine. Try extracting the arecoline with a
solvent that's immiscible with water (arecoline is soluble in chloroform; that might work). The only trouble is that arecoline is very water-soluble,
so you'd need a lot of salt in the water to drive it into the organic phase. |
Chloroform is difficult for me to obtain, any other suggestions for solvents? DCM failed so badly (arecoline solubility was shit) I think it might
have been a mistake in the article.
Regarding freebasing with NaOH - could it work with a weak solution? I found an article with this procedure -
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The free base of arecoline was prepared and purified by repeated extraction of aqueous arecoline hydrobromide solution (adjusted to pH 10 by 2M NaOH)
with petroleum ether [20]. All other chemicals and solvents were of analytical reagent grade. (Formulation optimization of arecoline patches,Pao-Chu
Wu et al)
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Crowfjord
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I don't see why using sodium hydroxide solution should be a problem. You can minimize ester hydrolysis by basifying slowly with good mixing, keeping
the solution cool during addition of hydroxide, and extracting soon after the desired pH is reached.
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