2-Methyl-2-butanol → 2-Methyl-2-butanol acetate

Temperature

0 °C

To a solution of 2-methylbutan-2-ol (10 g, 113 mmol) in DCM (100 mL) was added DMAP (0.693 g, 5.67 mmol) and TEA (17.39 mL, 125 mmol). Mixture was then cooled to 0° C. and acetic anhydride (15.56 mL, 125 mmol) was added and the mixture was stirred at room temp for 24 h. The mixture was then washed with sat.NaHCO3 (100 mL), 1N HCl (100 mL), 10% NaOH (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated to afford dark oil which was dilstilled by short path distillation (product distilled at 90-95° C.) to afford tert-pentyl acetate (8 g, 61.5 mmol, 54.2% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.98 (s, 3H), 1.78 (q, J=7.5 Hz, 2H), 1.43 (s, 6H), 0.89 (t, J=7.5 Hz, 3H).

1. washThe mixture was then washed
2. dry with materialNaHCO3 (100 mL), 1N HCl (100 mL), 10% NaOH (100 mL), brine (100 mL), dried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated
5. customto afford dark oil which
6. distillationwas dilstilled by short path distillation (product distilled at 90-95° C.)

ORD record

ord-6bde522315784515b9ef543067d7537a

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906929B2