Glycerol → 2,2-Bis(trifluoromethyl)-4-hydroxymethyl-1,3-dioxolane

In a 4 L round bottom flask, hexafluoroacetone (99.7 g; 0.6 moles) was condensed at 0° C. into a well stirred solution of glycerol (55.3 g; 0.6 moles) in 500 mL of anhydrous ethylene glycol dimethyl ether. After the addition of hexafluoroacetone was complete, the solution was allowed to warmn to ambient temperature. Next, a solution of 1,3-dieyclohexylcarbodiimide (136.2 g; 0.66 moles) in 2 L of anhydrous ethylene glycol dimethyl ether was added slowly to the resulting hemiketal solution over a period of about one and a half hours. The combined solution was stirred for an additional hour and then the low boiling solvent was removed using a rotary evaporator. The remaining liquid was transferred to a 250 mL round bottom flask and the liquid heated with stirring at 100° C. for 1 hour. While continuing to heat the liquid, the product was isolated by vacuum distillation at 76° C. and 18 mm of Hg. The yield of product was 117 g which is 81% of the theoretical value.

1. customcondensed at 0° C. into a well
2. customto warmn to ambient temperature
3. customthe low boiling solvent was removed
4. customa rotary evaporator
5. customThe remaining liquid was transferred to a 250 mL round bottom flask
6. temperaturethe liquid heated
7. stirringwith stirring at 100° C. for 1 hour
8. temperatureto heat the liquid
9. customthe product was isolated by vacuum distillation at 76° C.

ORD record

ord-da05c9d2837d40899a03fa36070770e3

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06231655B1