Methyl iodide → 1-Methylcyclohexane-1-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A flame-dried 500-mL round-bottomed flask capped with a rubber septum was charged with anhydrous CH2Cl2 (150 mL) via cannula and cyclohexanecarboxaldehyde (12) (9.09 mL, 75 mmol, 1.0 equiv) via syringe under N2. The flask was cooled in an ice bath for 10 min, the septum was removed, and t-BuOK (10.9 g, 97.5 mmol, 1.3 equiv) was added in one portion with rapid stirring. The septum was replaced, and iodomethane (14.0 mL, 225 mmol, 3.0 equiv) was added in one portion via syringe. The mixture was stirred at 0° C. under N2 for 30 min. The mixture was then allowed to warm to room temperature and stirred an additional 2 h. The resulting pale yellow, heterogeneous mixture was filtered through a 10-cm diameter medium porosity fritted disk funnel, and the cake was washed with CH2Cl2 (3×15 mL). The filtrate was washed with brine (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was distilled under reduced pressure (1 torr) while maintaining the receiving flask between −20 to −40° C. (bp <30° C.). The distillate was a clear, colorless oil that contained (1-methyl)cyclohexanecarboxaldehyde (13) and 1.25 equiv CH2Cl2, as determined by 1H-NMR analysis: 13.2 g total, ˜7.2 g (1-methyl)cyclohexanecarboxaldehyde (57 mmol, 76% yield). The product was used in the next step without further purification.

Provenance & Evidence