Preparation of Geminal Diacylates (Acylals) of Aldehydes – Scope and Reactivity of Aldehydes with Acid Anhydrides

Abstract

The geminal diacylates of a variety of aldehydes were prepared in good yields without any catalysts or solvent by simply refluxing the aldehydes with aliphatic acid anhydrides. The scope of the reactions and relative reactivities of aldehydes and acid anhydrides were examined.

1,1-Diacyloxy-1-phenylmethanes as versatile N-acylating agents for amines

“…99 -101 °C, [α]D 20 = -52 (c 1.0, CHCl3). 1 Phenylmethylene dipropionate 7a 31 General procedure B was followed to afford the title compound as a clear oil in 97% yield (2.15 g, 9.12 mmol). 1 H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H, CH(OCOEt)2), 7.51 (qd, J = 3.8, 1.5 Hz, 2H, ArH), 7.41 (ddt, J = 4.3, 3.1, 1.6 Hz, 3H, ArH), 2.40 (tt, J = 7.4, 3.6 Hz, 4H, 2 x CH2CH3), 1.16 (t, J = 7.5 Hz, 6H, 2 x CH2CH3).…”