organic chemistry - How can 2-indanone be prepared?

How do I prepare 2-indanone?

Would adding phosgene to ortho-xylene lead to the formation of 2-indanone?

Answer

If you want to start from ortho-xylene 1 I would recommend dibromination using N-bromosuccinimide to obtaining ortho-di(bromomethyl)benzene 2, followed by the addition of 1,3-dithianide anion 3 (prepared from formaldehyde and 1,2-ethanedithiol followed by treatment with NaH). While formaldehyde is electrophylic, 1,3-dithiane is nucleophylic if deprotonated (eg. with NaH, forming 1,3-dithianide ion) and can attack on the bromomethyl side of the molecule to get 4. This polarity inversion is called umpolung. A second treatment with NaH gives the cyclized product 5. Deprotection of the thioacetal gives 2-indanone 6. With this reversed polarity approach no phosgene is needed for the synthesis.