How to make 2-hydroxyacetophenone?

[Dr_Heckyll]

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.


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[Cyrax]

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]

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]

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

OMG! These druggies are converting tear gas into drugs!
I'm not fat just horizontally disproportionate.