Ammonium Chloride → Ethyl 4-hydroxy-4-methylcyclohexane-1-carboxylate

To a solution of ethyl 4-oxocyclohexanecarboxylate (4.00 g, 23.5 mmol) in diethyl ether (80 mL) was added MeLi (37.6 mL, 1M in diethyl ether) at −60° C. under nitrogen atmosphere. The reaction mixture was stirred at −60° C. for 30 min. Saturated aqueous NH4Cl (50 mL) was added and the resulting mixture was extracted with EtOAc (100 mL×2). The combined organic layers were washed with brine (150 mL) and water (150 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1) to afford ethyl 4-hydroxy-4-methylcyclohexanecarboxylate (1.8 g, 41% yield) as an oil.

1. extractionthe resulting mixture was extracted with EtOAc (100 mL×2)
2. washThe combined organic layers were washed with brine (150 mL) and water (150 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated
5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1)

ORD record

ord-5683a11f2fe443e6839b40159d080476

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434761B2