Formic Acid → 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one

Temperature

12.5 °C

To a solution of 4-chloromethyl-5methyl-1,3-dioxol-2-one (50 g) in acetonitrile (500 ml), formic acid (45 g) was added at 20-25° C. and the reaction mass cool to 10-15° C. followed by addition of triethylamine (95 g). Reaction mass was heated to 60-65° C. and stirred at the same temperature for about 5-6 hrs. Reaction mass was cooled to 15-20° C., filtered and washed by acetonitrile. Filtrate was taken and acetonitrile was distilled out under vacuum to concentrate the solution. Reaction mass was cooled to 25-30° C. and ethyl acetate and water was added, followed by stirring for about 15-20 minutes at 25-30° C. Aqueous layer extracted with ethyl acetate and combined organic layer were washed with brine solution. Organic layer was separated and evaporated completely under vacuum below 35-40° C. To the oily mass, methanol was added and heated to reflux temperature. A solution of HCl in isopropyl alcohol was added and the resulting solution was refluxed for about 60-75 mins. Reaction mass was cooled to 30-35° C. Distilled out the solvent completely to obtain title compound as oily mass. (Yield: 34.6 g; 79%)

1. customReaction mass
2. temperaturewas heated to 60-65° C.
3. customReaction mass
4. temperaturewas cooled to 15-20° C.
5. filtrationfiltered
6. washwashed by acetonitrile
7. distillationacetonitrile was distilled out under vacuum
8. concentrationto concentrate the solution
9. customReaction mass
10. temperaturewas cooled to 25-30° C.
11. stirringby stirring for about 15-20 minutes at 25-30° C
12. extractionAqueous layer extracted with ethyl acetate and combined organic layer
13. washwere washed with brine solution
14. customOrganic layer was separated
15. customevaporated completely under vacuum below 35-40° C
16. additionTo the oily mass, methanol was added
17. temperatureheated
18. temperatureto reflux temperature
19. additionA solution of HCl in isopropyl alcohol was added
20. temperaturethe resulting solution was refluxed for about 60-75 mins
21. customReaction mass
22. temperaturewas cooled to 30-35° C
23. distillationDistilled out the solvent completely

ORD record

ord-ed29bc4c292d46be999f7ea062f472d9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233955B2