Acetylation of 1-Methylcyclohexanol - DMAP as Catalyst

W. Steglich and G. Hoefle, Angew. Chem. Int. Ed. Engl. 8, 981 (1969)

1. Acetic anhydride (20 mL, 0.21 mol) is added with stirring to 1-methylcyclohexanol (11.4 g, 0.1 mol), DMAP (0.5 g, 4.1 mmol), and triethylamine (20 mL, 0.15 mol).

2. The mixture is allowed to stand at room temperature for 17 h.

3. The reaction mixture is worked-up by initially adding water, followed by sodium carbonate until carbon dioxide evolution ceases and the aqueous layer remains basic.  The organic layer is extracted with chloroform, dried over anhydrous sodium carbonate, and the solvent removed to give the crude product.  Distillation at a®ospheric pressure (b.p. 176°C) affords 1-methylcyclohexyl acetate (13.7 g, 88% yield).