Oxygen → 2-Indanone

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

(The following representative procedure is taken from Ragan et al., Org. Process Res. Dev. 2003, 7, 155–160). 2-Vinyl-indan-2-ol (15.0 g, 93.6 mmol) was dissolved in 150 mL MeOH, cooled to −78° C., and treated with a stream of ozone generated from O2. The dark solution became lighter in color after ca. 15 min, and HPLC analysis indicated consumption of starting material. Oxygen was bubbled through the solution for 5 min, then a stream of nitrogen was bubbled through for 30 min. A slurry of NaHSO3 (19.5 g, 187 mmol) in 15 mL water was then added, and the mixture was allowed to gradually warm to room temperature. After 30 min, a starch-Kl strip tested negative for peroxides. The slurry was then heated to 60° C. for 30 min to complete formation of the bisulfite adduct. After cooling to room temperature and stirring for 2 h, the resulting solids were collected and rinsed with methanol (2×30 mL), to provide the desired product as a while powder (16.2 g, 61% yield from 2-indanone). Combustion analysis of this material indicated 56% purity (Anal. Calcd for C10H11SO5Na: C, 45.1; H, 4.2. Found: C, 25.2; H, 2.6). Recrystallization from 10 volumes of water provided analytically pure material in 47% recovery (8.01 g recrystallized from 80 mL water, isolated 3.75 g analytically pure 2):

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