Author Topic: Resolution of Racemic Pseudoephedrine  (Read 99 times)

Hector2000

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Resolution of Racemic Pseudoephedrine
« on: October 22, 2012, 01:54:03 PM »
Resolution of racemic ephedrine(d,l-ephedrine) will be done by d-mandelic acid but what about pseudoephedrine? d-mandelic acid is usable for it?

Quote
Resolution of dl-Ephedrine.—A mixture of 13.8 g. of dl-ephedrine and 7.7 g. of d-mandelic
acid was dissolved in 30 cc. of hot 95% alcohol. On cooling the d-ephedrin-d-
mandelate crystallized out. After two recrystallizations from a small volume of alcohol
the product consisted of colorless, rhombic plates, melting at 170° with previous
sintering at 167°. The combined mother liquor yielded a further small amount of this
product. The salt as thus obtained was basified with potassium hydroxide and the base
was extracted with ether. The ethereal solution was evaporated to a small volume and
treated with alcoholic hydrogen chloride. The d-ephedrine hydrochloride as thus obtained
melted at 218 to 218.5°.
The mother liquor from the mandelate of the d-base was basified and the.extracted
base treated with 7.7 g. of l-mandelic acid. The crystalline mandelate was twice
recrystallized from a small volume of alcohol; m. p. 170° with previous sintering at
167°. The l-ephedrine hydrochloride obtained from the mandelate melted at 218 to
218.5°, alone or admixed with a purified specimen from Ma Huang.
It was now possible to obtain a further amount of d- and then l-base from the
mother liquor from the mandelate crystallizations by alternate treatment with d- and
l-mandelic acid, respectively.
« Last Edit: October 22, 2012, 02:00:09 PM by Hector2000 »

wasabi

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Re: Resolution of Racemic Pseudoephedrine
« Reply #1 on: October 23, 2012, 06:38:16 AM »
Any reason you want to resolve a particular diastereomer?

It might be a coveted collector's item but you don't need to if you just want to further your research to, maybe, the desoxy derivative?

Hector2000

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Re: Resolution of Racemic Pseudoephedrine
« Reply #2 on: October 24, 2012, 07:21:13 AM »
I made Ephedrine isomers (+,- Ephedrine - +,- Pseudoephedrine)
(by below proccess:
http://www.erowid.org/archive/rhodium/chemistry/nor-pseudo-ephedrine.html
just i used tetrahedron letters for methylation step)
and successfully i separated Pseudoephedrine by oxalic acid.
Now i have +,- Pseudoephedrine and  want to separate dextro(+)(1S,2S) enantiomer from levo(-)(1R,2R)
« Last Edit: October 24, 2012, 07:23:27 AM by Hector2000 »