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

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##

1. customCompound 17 was prepared by the method
2. temperaturethe temperature was maintained below 30° C
3. stirringThe mixture was stirred at room temperature for 12 hours
4. customthe temperature below 40° C
5. customThe organic fraction was separated
6. extractionthe aqueous phase was extracted several times with dichloromethane
7. dry with materialThe combined organic fractions were dried (MgSO4)
8. customevaporated
9. distillationthe oily residue was distilled under vacuum

ORD record

ord-5ec50cbe4154408a934d250bcc27c2cd

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05567783