Methanol → 5-Chloro-2-cyclohexyl-valeric acid

Temperature

60 °C

A 5 N sodium hydroxide solution (2.5 ml) was added to a solution of methyl 5-chloro-2-cyclohexyl-valerate (1.00 g) in THF (3 ml)-methanol (6 ml). The reaction solution was stirred at room temperature for six hours and at 60° C. for further two hours. After allowing the reaction solution to cool, water and diethyl ether were added to the reaction solution, and the aqueous layer was separated. 5 N hydrochloric acid (2.6 ml) and ethyl acetate were added to the aqueous layer, and the organic layer was separated. The ethyl acetate extraction layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 5-chloro-2-cyclohexyl-valeric acid (287 mg).

1. temperatureto cool
2. customthe aqueous layer was separated
3. addition5 N hydrochloric acid (2.6 ml) and ethyl acetate were added to the aqueous layer
4. customthe organic layer was separated
5. extractionThe ethyl acetate extraction layer
6. washwas washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

ORD record

ord-c0a60c69c739448980f831f0f726b8ee

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935815B2