Sciencemadness Discussion Board

"Friendly" synthesis of Benzyl Dimethyl Carbinol

EvlRenne - 6-10-2018 at 07:22

Dear all,

chemistry was always the point of interest of mine, I wanted to do some organic synthesis, I was searching in the web for "friendly" route to synthesis Benzyl Dimethyl Carbinol (CAS 100-86-7).
I can buy it in China, but price for the delivery is ridiculous and concern about quality.
I want to do it by myself, not only because of price, but curiosity.


CuReUS - 6-10-2018 at 07:43

just do a grignard reaction between benzyl bromide and acetone

fusso - 6-10-2018 at 07:58

I think this could be a candidate for the tert alcohol catalyst in making Na.

[Edited on 06/10/18 by fusso]

EvlRenne - 6-10-2018 at 10:15

I was thinking about following:
C7H7Cl + Mg + Et2O(Anh) + C3H6O(Anh) + NH4Cl and dry it over K2CO3.
Any suggestion?

Tsjerk - 6-10-2018 at 11:30

I would call a grignard "friendly" quite the opposite

EvlRenne - 6-10-2018 at 12:29

Quote: Originally posted by Tsjerk  
I would call a grignard "friendly" quite the opposite

I agree, I think I will not be able even start it

fusso - 6-10-2018 at 12:33

Why you want a "friendly" synthesis? How do you define friendly?

EvlRenne - 6-10-2018 at 12:40

Quote: Originally posted by fusso  
Why you want a "friendly" synthesis? How do you define friendly?

Friendly - synthesis which is not require some high-end lab equipment, very complicated steps with special conditions (like hight pressure, hight temp. and so on), and working with dangerous, but not deadly chemicals.

fusso - 6-10-2018 at 12:46

Quote: Originally posted by EvlRenne  
I was thinking about following:
C7H7Cl + Mg + Et2O(Anh) + C3H6O(Anh) + NH4Cl and dry it over K2CO3.
Any suggestion?
Then I think that's friendly enough?

Metacelsus - 6-10-2018 at 23:20

What about reacting phenyl-2-propanone with dimethylzinc?

:D

More seriously, the Barbier reaction might be an option. (Benzyl bromide + zinc powder + acetone)

Tsjerk - 6-10-2018 at 23:24

Quote: Originally posted by fusso  
Quote: Originally posted by EvlRenne  
I was thinking about following:
C7H7Cl + Mg + Et2O(Anh) + C3H6O(Anh) + NH4Cl and dry it over K2CO3.
Any suggestion?
Then I think that's friendly enough?


Friendly also includes doable for a beginner, have you ever done a grignard?

CuReUS - 7-10-2018 at 01:29

Quote: Originally posted by Metacelsus  
More seriously, the Barbier reaction might be an option. (Benzyl bromide + zinc powder + acetone)
Yes,that's a much better idea :)
I had heard about the barbier reaction but I didn't know you could do it with Mg or Zn too :o

I think you could use benzyl chloride as well
using Mg -https://gallica.bnf.fr/ark:/12148/bpt6k30841/f111.pleinepage...

using Zn -https://www.organic-chemistry.org/abstracts/lit1/029.shtm