Ethyl Acetate → 2-{Hydroxy-(3-methoxyphenyl)methyl}cyclooctanone

Participants

Reaction Steps

To a solution of cyclooctanone (4.0 g) in THF (40 ml) was added LDA (23 ml, 1.5M solution in cyclohexane) at -78° C. under N2, and then after 30 minutes, a solution of m-anisaldehyde (4.1 g) in THF (10 ml) was added in the solution. After being stirred for 2 hours at the same temperature, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 2-{hydroxy-(3-methoxyphenyl)methyl}cyclooctanone (6.9 g). MS (m/z): 245 (M+ -17) IR (Neat): 3400, 1690 cm-1NMR (CDCl3, δ): 1.0-2.3 (10H, m), 2.8-3.2 (2H, m), 3.3-3.6 (1H, m), 3.79 (3H, s), 4.8-5.0 (1H, m), 6.7-7.0 (3H, m), 7.1-7.3 (1H, m)

Provenance & Evidence