java (Hive Bee)
07-07-03 14:31
No 445324
       Question about Acids for Chlorination  Bookmark   

In trying to make an chlorinate the OH with Phosphorus oxy chloride  will this  work the solvents dichloromethane or chloroform in the making of chloroephedrine?  As thionyl chloride becomes less available and methods to synthesise are not to friendly , there is  a need to find alternatives. I used the search engine and read halfpint version of synthesis and also in the synthesis or LSD, where in the acid chloride step they used this compund,(phosphorous oxy chloride).

So to re-phrase my question will the Phosphorous oxychloride react well in chloroform or dichloromethane as solvent, in the synthesis of the chloroephedrine?.....java

Edited: some editing done to correct some terms
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    Aurelius
(Active Asperger Archivist)
07-07-03 15:43
No 445350
       Chlorinated Solvents  Bookmark   

"good solubility in benzene, carbon disulfide, chloroform and carbon tetrachloride and can itself be used as a solvent"

Chlorinated solvents are best, but you should make sure that there is good solubility before using DCM.

http://www.bayertextile.com/product/pages/chemicals/pdf/phosphorus_oxychloride.pdf
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    Rhodium
(Chief Bee)
07-07-03 17:07
No 445378
       acid chloride?  Bookmark   

I'm sorry to interrupt, but what use do you have of an acid chloride in the synthesis of chloroephedrine? 		 
 
 
 
    java
(Hive Bee)
07-07-03 18:17
No 445395
       RE" Question about acids for chlorination...  Bookmark   

Rhodium,
Perhaps by calling acid chlorides when I just chlorinate the OH group should just be chloroephedrine?  C6H5CH(OCl)CH(NHCH3)CH3, however I'm was needing information on  acids  for the chlorination of OH as the use thionyl chloride is adequate,but because of the scarcity and problems with it I was inquiring about the Phosphorous -oxy -chloride.  Maybe that is the misuse of the term that caused the confussion.......java

Note: I've corrected the misleading term used on the post , thanks
We're  all in this world together,
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    Rhodium
(Chief Bee)
07-07-03 19:02
No 445409
       Chloroephedrine formula
(Rated as: good read) 		 Bookmark   

Chloroephedrine (from chlorination of Ephedrine) is an alkyl chloride and nothing else, and the formula is not C6H5-CH(OCl)CH(NHCH3)CH3 (this would constitute an alkyl hypochlorite, and would be very reactive/unstable), it is rather C6H5-CHClCH(NHCH3)CH3

Here are a few links about Chloroephedrine:

Post 392817 (Rhodium: "Toxicity of chloropseudoephedrine/chloroephedrine", Stimulants)
Post 401416 (Rhodium: "Hermann Emde's Ephedrine Chemistry Treatise", Stimulants) 		 
 
 
 
    java
(Hive Bee)
07-07-03 20:44
No 445433
       Re: Question about Acids for Chlorination  Bookmark   

Rhodium, thanks for the clarification on the action of thionyl chloride with the OH group found in ephedrine. Somehow all this time I thought it was making an OCl from the OH to making it a better leaving group when I hydrogenated and reduced it to the alkane. So the phosphorous oxy chloride will do the same to the OH and make the alkyl chloride.....it will make a good replacement since most of the PCl5, PCl3 are watched .......java
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    Rhodium
(Chief Bee)
07-09-03 07:07
No 445863
       Phosphorous oxychloride is watched  Bookmark   

POCl3 is indeed also watched, as it has uses in the synthesis of warfare agents in the Sarin/Tabun family.