Acetic Acid → 3-(2-Oxo-1-phenylcyclohexyl)propanoic acid

Beteiligte Stoffe

Reaktionsschritte

A mixture of 3-(2-oxo-1-phenylcyclohexyl)propanenitrile (5.05 g, 22.22 mmol) in acetic acid (11.1 mL), conc. HCl (33.2 mL), and water (11.1 mL) was refluxed for 16 h under N2, cooled to room temperature, and poured into water (66 mL). The product separated out as an layer of oil. The suspension was cooled to 0° C. in an ice bath for 30 min. with occasional swirling and the crystallized product was collected by filtration and rinsed several times with water, and dried in vacuo to obtain 3-(2-oxo-1-phenylcyclohexyl)propanoic acid (1B, 4.77 g, 85% yield) as a white crystalline solid. HPLC: tR=2.47 min, YMC Combiscreen ODS-A 4.6×50 mm, 4 min gradient, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH—0.1% TFA; Final solvent: 90% aq. MeOH—0.1% TFA. LC/MS: m/e 247.2 (M+H)+, 229.2 (M+H−H2O)+.

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