The Friedel-Kraft抯 reaction of 2-isopropylindan (I) with ethyloxalyl chloride (II) by means of AlCl3 in methylene chloride gives ethyl 2-(2-isopropyl-5-indanyl)-2-oxoacetate (III), which is hydrolyzed with NaOH in refluxing ethanol to the corresponding free acid (IV). The reaction of (IV) with methylmagnesium iodide in ether yields 2-(2-isopropyl-5-indanyl)-2-hydroxypropionic acid (V), which is dehydrated with H2SO4 in refluxing dioxane affording 2-(2-isopropyl-5-indanyl)acrylic acid (VI) (1,2,4). Finally this compound is reduced with H2 over Raney-Ni or Pd/C in methanol or dioxane
The Friedel-Kraft抯 reaction of 2-isopropylindan (I) with acetic anhydride in methylene chloride gives 2-isopropyl-5-acetylindan (VII), which by with sulfur and morpholine (A) at 140 C gives 2-(2-isopropyl-5-indanyl)acetylmorpholinothioamide (XI), which is hydrolyzed to 2-(2-isopropyl-5-indanyl)acetic acid (XII). The esterification of (XII) with ethanol - H2SO4 yields the corresponding ethyl ester (XIII), which is condensed with diethyl carbonate (XIV) by means of sodium ethoxide in refluxing ethanol affording diethyl (2-isopropyl-5-indanyl)malonate (XV), which is methylated with methyl iodide and sodium ethoxide in refluxing ethanol to give diethyl methyl-(2-isopropyl-5-indanyl)malonate (XVI). Finally this compound is hydrolyzed and decarboxylated by treatment with NaOH in refluxing hydrazine hydrate Compound (XII) can also be obtained by a Wolf-Kistner reduction of ketoacid (IV) in refluxing hydrazine hydrate
The Friedel-Kraft抯 reaction of 2-isopropylindan (I) with acetic anhydride in methylene chloride gives 2-isopropyl-5-acetylindan (VII), which is reduced with KBH4 in methanol yielding 2-isopropyl-5-(1-hydroxyethyl)indan (VIII). The treatment of (VIII) with SOCl2 in benzene affords 2-isopropyl-5-(1-chloroethyl)indan (IX), which by reaction with NaCN in hot HMPA yields 2-(2-isopropyl-5-indanyl)propionitrile (X). Finally this compound is hydrolyzed with H2SO4 in refluxing acetic acid - water