Synthesis
The general procedure for the synthesis of 2,3-dihydro-1H-4-indanol from 4-hydroxy-1-indanone was as follows: NaCNBH3 (6.4 g, 101.1 mmol) was added to a mixture of 4-hydroxy-1-indanone (5.0 g, 33.7 mmol) and zinc iodide (32.3 g, 101.1 mmol) in ethylene chloride (100 mL). The reaction mixture was stirred under reflux conditions for 2 hours. After completion of the reaction, it was filtered through silica gel (SiO2) while hot and eluted with dichloroethane. The filtrate was collected and concentrated under reduced pressure. The residue was dissolved in ether and filtered to remove the resulting white precipitate. The filtrate was collected again, concentrated in vacuum and finally purified by fast column chromatography to afford the target product 2,3-dihydro-1H-4-indanol (3 g, yield: 66%). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.02 (m, 1H), 6.80 (d, J = 5.2 Hz, 1H), 6.61 (m, 1H), 2.91 (m, 4H), 2.05 (m, 2H).
References
[1] Patent: US2011/152246, 2011, A1. Location in patent: Page/Page column 118-119
[2] Patent: CN108997163, 2018, A. Location in patent: Paragraph 0094; 0098; 0099
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4625 - 4629
[4] Patent: US2003/207916, 2003, A1
[5] Patent: US2004/209936, 2004, A1
