Propose a synthesis of indane from benzene
To prepare indane (6) from benzene, make the procedure as simple as possible and amenable to scale-up. Propiophenone (2) is readily available by Friedel-Crafts acylation of benzene with propionyl chloride (1). Removal of the carbonyl group of propiophenone and the creation of a carboxyl moiety can be achieved via the Willgerodt reaction to produce amide 3. Vigorous  acid or base cleavage of the amide is possible but nitrous acid affords a mild route to carboxylic acid 4. One can use the AlCl3 F-C route again but hot polyphosphoric acid is a clean method for the intramolecular acylation without having to form the acid chloride. Finally, Clemmensen reduction of indanone (5) gives indane (6). Wolff-Kishner reduction is also a good option for the final step.