The Vespiary

The Hive => Methods Discourse => Topic started by: Natrix on September 24, 2001, 10:44:00 PM

Title: Cl -> OH
Post by: Natrix on September 24, 2001, 10:44:00 PM

How difficult would it be to make 2-methyl-hydrochinone from 4-chloro-3-methylphenol (PCMC) ? PCMC is a biocide and is used against bacteria, fungi and yeast.
 
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Title: Re: Cl -> OH
Post by: PolytheneSam on September 24, 2001, 11:12:00 PM

I saw something in a chemistry book about a Dow Chemical process for making phenol from chlorobenzene using NaOH solution at 350 degrees C under pressure.

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Title: Re: Cl -> OH
Post by: Rhodium on September 24, 2001, 11:13:00 PM

Reflux in strong sodium hydroxide solution together with copper powder, for at least 24h.

A general method is described for 5-hydroxyvanillin in:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html)

If you were planning on using it for 2,5-dimethoxytoluene, I'd suggest you methylate the starting material first, for easier workup, and possibly better yields.

Title: Re: Cl -> OH
Post by: Natrix on September 25, 2001, 12:22:00 PM

Thanks for your answers PolytheneSam and Rhodium.  Although the yield might be low (US.P. 3,778,481), the substance is very interesting because it is sold otc and it is inexpensive. 

Title: Re: Cl -> OH
Post by: foxy2 on September 25, 2001, 05:40:00 PM

If you have access to an ultrs sonic bath I would put the reaction in it periodically.  It should increase yeilds

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