Hydrochloric Acid → 1-(2-Ethyl-butyl)-cyclohexanecarboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (2.37 g, 23.4 mmol) in THF (12 mL) 1.6 M n-BuLi in hexane (13.2 mL, 21.09 mmol) was added with stirring over 20 min at −65° C. The suspension was warmed up to −40° C. and then added via a teflon tube over 15 min to a stirred solution of cyclohexanecarboxylic acid methyl ester (2.0 g, 14.1 mmol) in THF (20 mL) at −65° C. The resulting yellow solution was stirred 10 min at −65° C., then it was added over 30 min to a solution of 1-bromo-2-ethylbutane (3.714 g, 22.5 mmol) in THF (10 mL) at 0° C. The solution was stirred 1 h at 0° C. and then overnight without a cooling bath while warming up to room temperature. At 5° C. ice-water (15 mL) was added, followed by 2N HCl (30 mL). The organic phase was diluted with ethyl acetate and washed with sat. aq. NaHCO3 and with aq. NaCl. The aqueous phases were extracted with ethyl acetate. The organic phases were combined, dried over sodium sulfate and concentrated. The crude product (3.3 g) was distilled at 45° C. (0.01 mbar) to give 2.1 g (66%) 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid methyl ester as a colorless oil, purity 92.5% (GC area). The structure of the title compound was confirmed by GC-MS (M=226).

Provenance & Evidence