Hydrochloric Acid → 5-Hydroxy-1-indanone

Participants

Reaction Steps

5-Methoxy-indan-1-one (8 g, 49.3 mmol), and 4-tert-butyl-2-methyl-benzenethiol sodium salt (11.92 g, 59.2 mmol) were heated at 142° C. for 1 hr under argon. After cooling to RT, water (80 ml) was added followed by 1N HCl (80 ml) and EtOAc (120 ml). The mixture was shaken and the aqueous phase extracted with EtOAc (100 ml), the combined organic extracts were washed with satd.NaCl solution (100 ml) and dried with Na2SO4, filtered and evaporated. The residue was chomatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (2:3), producing 5-hydroxy-indan-1-one (3.55g, 22.6 mmol, 45.9 %) as orange crystals Mp. 185-187° C., MS m/e=148.2 (M+).

Provenance & Evidence