Formic Acid → 3-Tert-butoxy-1,2-propanediol

Participants

Reaction Steps

Compound 17 was prepared by the method described by Montanari and Tundo (Montanari, F. and Tundo, P., J. Org. Chem. 1982, 47, 1298). tert-Butyl glycidyl ether (Aldrich), (141 ml, 1.0 mol.) was added dropwise to 99% formic acid (83 ml, 2.2 mol). The reaction mixture was stirred and the temperature was maintained below 30° C. The mixture was stirred at room temperature for 12 hours. A solution of sodium hydroxide (100 g, 2.5 mol.) in 125 ml of water was added slowly, keeping the temperature below 40° C. The organic fraction was separated and the aqueous phase was extracted several times with dichloromethane. The combined organic fractions were dried (MgSO4) and evaporated and the oily residue was distilled under vacuum to give 17 (75 g, 54%) as a colorless oil: (bpt. 55°-60° C., 0.015 torr): IR 3400 (OH) cm-1 ; 1H-NMR (CDCl3) d (ppm) 3.25-4.0 (m, 7H), 1.2 (s, 9H); 13C-NMR (CDCl3) d (ppm) 73.5, 70.5, 64.4, 63.6, and 27.16. Mass spectrosocopy, m/e: 148 M+ base peak (Scheme 3). ##STR5##

Provenance & Evidence