| Pages:
1
2 |
DraconicAcid
International Hazard
Posts: 4333
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline
Mood: Semi-victorious.
|
|
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.
|
|
|
bfesser
|
Threads Merged
30-1-2014 at 09:55 |
metalayer
Harmless
Posts: 23
Registered: 7-7-2013
Member Is Offline
Mood: No Mood
|
|
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 -
| Quote: |
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)
|
|
|
|
Crowfjord
Hazard to Others
Posts: 390
Registered: 20-1-2013
Location: Pacific Northwest
Member Is Offline
Mood: Ever so slowly crystallizing...
|
|
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.
|
|
|
| Pages:
1
2 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
