Hydrochloric Acid → alpha-Oxocyclohexaneacetic acid

Temperature

60 °C

To a solution of ethyl cyclohexyloxoacetate (46 g) in MeOH (25 mL) was added water (60 mL) and NaOH (50% 20 mL) at 0-15° C. The reaction mixture was heated to 60° C. for 1.5 h. The reaction mixture was cooled with ice-water bath, and acidified with 15% HCl till pH 1. The mixture was extracted with ethyl acetate (2×250 mL). The extracts were washed with brine, dried with sodium sulfate. The drying agent was removed by filtration and the solvent was removed to give a low melting solid (39 g, 99%). 1H NMR: δ 1.15-1.40 (m, 5H,), 1.62-1.96 (m, 5H). 3.20 (m, 1H), 9.4 (s, 1H). 13C-NMR δ, 25.93, 25.76, 27.89, 45.04, 160.90, 198.29.

1. temperatureThe reaction mixture was cooled with ice-water bath
2. extractionThe mixture was extracted with ethyl acetate (2×250 mL)
3. washThe extracts were washed with brine
4. dry with materialdried with sodium sulfate
5. customThe drying agent was removed by filtration
6. customthe solvent was removed

ORD record

ord-dcd8cbebc73e414fa1400d84c56ff23c

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06025177