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

Temperature

12.5 °C

4-Chloromethyl-5-methyl-1,3-dioxol-2-one (25 g) was dissolved in dichloromethane (250 ml) at 20-25° C., sodium iodide (2.5 g) and formic acid (22 g) was added at 20-25° C. Resulting mixture was cooled to 10-15° C. and triethyl amine (46.8 g) was added at 10-15° C. in 20-25 minutes. Resulting mixture was stirred for 5.0-6.0 hrs at 40-45° C., cooled to 20-25° C. and added DM water (250 ml). Organic layer was separated and washed with brine solution, and distilled out. Residue was dissolved in methanol (300 ml), methanolic HCl was added drop wise and resulting mixture was stirred for 1 hrs at 60-65° C. Active charcoal (1 g) was added to the reaction mass and stirred for 20-25 minutes at 50-55° C. Reaction mass was filtered through hyflo bed and bed was washed by MeOH (12 ml). The filtrate was evaporated under vacuum at 40-45° C. Obtained product was diluted with ethyl acetate (75 ml) and evaporated under vacuum to remove methanol content. (Yield: 0.67 g; 76.5%)

1. customResulting mixture
2. customResulting mixture
3. temperaturecooled to 20-25° C.
4. customOrganic layer was separated
5. washwashed with brine solution
6. distillationdistilled out
7. dissolutionResidue was dissolved in methanol (300 ml)
8. additionmethanolic HCl was added drop wise
9. customresulting mixture
10. stirringwas stirred for 1 hrs at 60-65° C
11. stirringstirred for 20-25 minutes at 50-55° C
12. customReaction mass
13. filtrationwas filtered through hyflo bed and bed
14. washwas washed by MeOH (12 ml)
15. customThe filtrate was evaporated under vacuum at 40-45° C
16. additionObtained product was diluted with ethyl acetate (75 ml)
17. customevaporated under vacuum
18. customto remove methanol content

ORD record

ord-47da0238647f4a99b0be90e894d0e6bc

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233955B2