Purification of alkyl halide from pyridine

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SUMMARY

This discussion focuses on the purification of alkyl halide, specifically pyrene 1-methylchloride, from a pyridine solution using thionyl chloride (SOCl2). The user initiated the reaction with 0.02 grams of pyrene 1-methanol, 20 mL of pyrene, and 200 µL of SOCl2 at room temperature. The proposed method for purification involves solvent evaporation, but the user seeks alternative separation techniques and guidance on modifying pyrene 1-methylchloride to a thiol using thiolurea. Considerations for acid-base washing are also mentioned.

PREREQUISITES
  • Understanding of alkyl halide synthesis and purification techniques
  • Familiarity with thionyl chloride (SOCl2) and its applications
  • Knowledge of thiol chemistry and thiolurea reactions
  • Basic principles of solvent evaporation and separation methods
NEXT STEPS
  • Research advanced separation techniques for alkyl halides, such as distillation or chromatography
  • Learn about the synthesis and properties of thiol compounds and their applications
  • Investigate the use of thiolurea in organic synthesis and its solvent requirements
  • Study acid-base extraction methods for purifying organic compounds
USEFUL FOR

Chemists, organic synthesis researchers, and students interested in alkyl halide purification and thiol modifications will benefit from this discussion.

ecnerwalc3321
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I am looking for a way to purify an alkyl halide from a pyridine solution. I started with
0.02 grams of pyrene 1-methanol and added to it 20 mL pyrene and 200 uL of SOCl2 at room temperature hoping that the substitution reaction would happen. The solution has been sitting for a day at room temperature as I am figuring out how to recover the
pyrene 1-methylchloride (?). The only method that I think of after reading is to let all the solvent evaporate and be left with the pyrene. I'm not well versed in separation techniques (not a chemist); does anyone have better suggestions?

Ultimately, I'm looking to modify the pyrene 1-methanol to be a thiol. After making the pyrene 1-methylchloride I was thinking about using thiolurea (with what solvent I don't know) to complete the modification. Does this method seem feasible? What are some considerations that I need to be aware of? Thanks for your input.
 
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Acid-base wash?
 

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