-1
$\begingroup$

I want to make 5-hydroxy-2-indanone, so I need make 5-nitro-2-indanone first.But I can find any documents for reference. please give me some suggestion, thanks

$\endgroup$
1
$\begingroup$

Drawing on Klaus's comment and reference to the preparation of 2-indanone, I suggest starting with the commercially available 3,4-dimethyl anisole. Bromination under radical conditions (non-polar solvent, AIBN, arc lamp) with NBS should give the bis-bromomethyl compound. Reaction with the anion of dithiane with 2eq of strong base should give the dithiane of 5-methoxy-2-indanone. Deprotection with boron tribromide reveals the OH and dithiane removal by acid hydrolysis or Hg++ gives 5-hydroxy-2-indanone.

$\endgroup$
  • $\begingroup$ From personal experience, 3,4-dimethylanisole may be activated enough to under electrophilic bromination even under nonpolar/radical conditions. $\endgroup$ – Ben Norris Mar 24 '17 at 0:02
  • $\begingroup$ it is nice for me to get some information about my question from your kind. but do you have any documents for me to refer to? because I need some documents in detail to start our work. please!! thanks in advance ,friends! $\endgroup$ – jacky Mar 27 '17 at 2:13

Not the answer you're looking for? Browse other questions tagged or ask your own question.