Re: Synthesis of 3,5 dimethoxy benzyl alcohol

Yabahoobs wrote:
On Mar 26, 5:22 pm, Anonymous Sender <anonym...@xxxxxxxxxxxxxxxxxxxxx>
wrote:
I've been asked to develop a means of synthesis of 3,5
dimethoxy benzyl alcohol. The meta-addition of the second
-OCH3 group is giving me trouble.

What is / are the common means of synthesis for this
compound ?

What is this? A homework problem? Synthesize FROM WHAT?
"From benzene, any organic reagent of two carbons or less,
and any inorganic reagent, design syntheses of the following
compounds ..."

If 3,5-(MeO)2-Ph-CH2OH was needed for a 'real lab', you
know that you'd just buy it; it's not expensive. If, for
some reason, you didn't want to buy it, there is another
even cheaper starting material (75 cents/gram from Aldrich)
that is only one (decent) step removed from the target.

But maybe you want an isotopic label in there. You could
design a complex synthesis for labeling every position.

When is the homework due?

The goal is to find 3 ways to get to the target from catechol or
phenol.

Here's one to get you rolling then...
1. Phenol to Bromobenzene (PBr5)
2. Bromobenzene to Benzoic Acid (Grignard + CO2)
3. Benzoic Acid to 3,5-Dihydroxybenzoic Acid (fuming H2SO4 - Org Synth)
4. 3,5-Dihydroxybenzoic Acid to 3,5-Dimethoxybenzoic Acid (Dimethyl
sulphate)
5. 3,5-Dimethoxybenzoic Acid to 3,5-Dimethoxybenyl Alcohol (LiAlH4 in THF
or BH3 in THF)



--
Ron Jones
Process Safety & Development Specialist
Don't repeat history, unreported chemical lab/plant near misses at
http://www.crhf.org.uk Only two things are certain: The universe and
human stupidity; and I'm not certain about the universe. ~ Albert
Einstein


.

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  • Re: Synthesis of 3,5 dimethoxy benzyl alcohol
    ... Synthesize FROM WHAT? ... design syntheses of the following ... that is only one step removed from the target. ...
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