(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol → 2,2-Dimethyl-1,3-dioxan-5-one

Participants

Reaction Conditions

Reaction Steps

To a water (1.5 L) solution of (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol (251 g, 1.57 mol) and KH2PO4 (213 g, 1.57 mol) at 0° C., a water solution (1.8 L) of NaIO4 (336 g, 1.57 mol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 hours and room temperature overnight. The product was extracted by CH2Cl2 (5×300 mL), dried over MgSO4 and distilled, yielding 2,2-Dimethyl-1,3-dioxan-5-one (153 g, 75%) as a colorless liquid, by 102° C./40 torr. 1H NMR (300 MHz, CDCl3) δ1.26 (s, 6H), 3.96 (s, 4H).

Provenance & Evidence