Solketal → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl acetate

Participants

Reaction Steps

To a solution of 28.1 g (212 mmol) of 2,2-dimethyl-1,3-dioxolane-4-methanol and 44 g (361 mmol) of DMAP in 1 L of dichloromethane was added 36 mL (382 mmol) of acetic anhydride dropwise. The resulting mixture was stirred at rt for 0.5 h. The reaction mixture was then quenched with NH4Cl (aq), the organic layer separated and washed with saturated NaHCO3. The organic layer was then dried (Na2SO4), filtered and concentrated in vacuo to give an oil which was used without further purification. 1H NMR (500 MHz, acetone-d6): δ 4.30-4.25 (m, 1H), 4.09-4.01 (m, 1H), 3.72 (dd, 1H), 2.01 (s, 3H), 1.33 (s, 3H), 1.27 (s, 3H).

Provenance & Evidence