4-Hydroxycyclohexanecarboxylic acid → 1-(4-Hydroxycyclohexyl)ethanone

Temperature

-78 °C

Methyllithium (1M in THF) (120 mL, 3.5 eq.) was added to a solution of 4-hydroxy-cyclohexanecarboxylic acid (cis/trans mixture) (5.00 g, 1 eq.) in THF (350 mL) at −78° C. After stirring at −78° C. for 45 min, the cooling bath was removed and the resulting mixture was warmed to room temperature and stirred overnight. After total 24 h, the resulting reaction mixture was poured into ice/water (800 mL). This mixture was vigorously stirred. The separated aqueous phase was extracted with MeOH/EtOAc (˜1/20). The combined organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (50% to 100% EtOAc/hexanes) to give 1-(4-hydroxy-cyclohexyl)-ethanone (2.08 g, 42%).

1. customthe cooling bath was removed
2. temperaturethe resulting mixture was warmed to room temperature
3. stirringstirred overnight
4. waitAfter total 24 h
5. customthe resulting reaction mixture
6. stirringThis mixture was vigorously stirred
7. extractionThe separated aqueous phase was extracted with MeOH/EtOAc (˜1/20)
8. dry with materialThe combined organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was purified by chromatography (50% to 100% EtOAc/hexanes)

ORD record

ord-ae87b9126d7c40779080b9b916682edf

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691814B2