The Vespiary
The Hive => Chemistry Discourse => Topic started by: Dr_Heckyll on July 23, 2002, 02:15:00 PM
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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.
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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?
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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.
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acetophenone ----> chloroacetophenone ---> desired product
OMG! These druggies are converting tear gas into drugs!
I'm not fat just horizontally disproportionate.