Methanol → 1,1,1,3,3,3-Hexafluoro-2-methoxy-2-propanol

Into 1.82 g of dry methanol was introduced 18.86 g of hexafluoroacetone, and the mixture was stirred at room temperature. After 6 hours, the reaction mixture was distilled under a reduced pressure, to obtain 11.2 g of hexafluoroacetone methylhemiacetal as an intermediate fluorinated hemiacetal. Next, in 50 mL of THF was dissolved 11.2 g of hexafluoroacetone methylhemiacetal, and the mixture was cooled to −78° C. To the solution was added dropwise 35.5 mL of a n-butyllithium solution in hexane (concentration: 1.6 mol/L). After stirring for one hour, 5.14 g of acryloyl chloride was added dropwise thereto. After stirring for 4 hours under ice cooling, precipitated lithium chloride was filtered off and the filtrate was concentrated in vacuo. To the residue was added 200 mL of ether, and the ethereal layer was sequentially washed with a saline solution and water. The ethereal layer was dried over anhydrous magnesium sulfate. After evaporation of ether under a reduced pressure, the residue was distilled under a reduced pressure to obtain 3.06 g of the desired acrylate 3 (yield: 21%, colorless liquid).

1. distillationthe reaction mixture was distilled under a reduced pressure

ORD record

ord-8450deae7d7c478b9e4b9ecf4a80d1a0

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07232639B2