Dr_Heckyll (Hive Bee)
07-23-02 14:15
No 336119
      How to make 2-hydroxyacetophenone?  Bookmark   

Any suggestions for short, efficient and cheap ways to prepare 2-hydroxyacetophenone [Ph-C(=O)-CH2-OH]? The compound is commercially available, but too expensive to be of use. Ring-substituted derivatives would also be of interest.



Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
 
 
 
 
    Cyrax
(Hive Bee)
07-23-02 14:35
No 336122
      Synthesis  Bookmark   

Any suggestions for short, efficient and cheap ways to prepare 2-hydroxyacetophenone [Ph-C(=O)-CH2-OH]?



First, we have to acylate benzene with benzyloxyacetylchloride: put dry benzene and anhydrous AlCl3 in a flask and add the acetylchloride, let react at 50 C

Then, we should remove the benzyl protecting group by catalytic hydrogenation with 0.5 weight eq. of 10 % Pd / C at 48 psi.

What can one do with this compound?
 
 
 
 
    Dr_Heckyll
(Hive Bee)
07-23-02 16:15
No 336128
      Interesting solution, Cyrax, but not quite ...  Bookmark   

Interesting solution, Cyrax, but not quite satisfying for two reasons: benzyloxyacetylchloride is expensive and not broadly available, and catalytic hydrogenations, especially under pressure, are not generally available in smaller labs.

The compound of interest can easily be converted to 4-phenyl-4-oxazolin-2-one and substituted analogues which might have some pharmacological activity.



Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
 
 
 
 
    Osmium
(Stoni's sexual toy)
07-23-02 17:26
No 336141
      acetophenone ----> chloroacetophenone ---> ...  Bookmark   

acetophenone ----> chloroacetophenone ---> desired product

OMG! These druggies are converting tear gas into drugs!

I'm not fat just horizontally disproportionate.