Ethylene Glycol → Ethyl 2-[4-hydroxy-2-oxabutyl]acrylate

To a solution of 32.52 g trifluoromethanesulphonic anhydride in 100 ml dichloromethane a solution of 15 g (0.115 mol) α-hydroxyethylacrylate and 11.66 g (0.115 mol) triethylamine in 200 ml dichloromethane was added slowly, so that the temperature of the reaction mixture stays below 5° C. The solution was added drop wise at room temperature to 210 g (1.127 mol) 1,2-ethandiol. After the reaction mixture was stirred for 12 h at room temperature the solution was successively washed with 1×200 ml water, 2×250 ml of an aqueous sodium carbonate solution (25 wt %) and 1×200 ml water. The organic layer was dried over magnesium sulphate and filtered. After the evaporation of the solvent the oily raw product was stabilized with 15 mg BHT and purified by vacuum distillation (63° C./0.032 mbar). This afforded 10.12 g (yield: 50%) of a clear, colorless oil.

1. customstays below 5° C
2. washwas successively washed with 1×200 ml water, 2×250 ml of an aqueous sodium carbonate solution (25 wt %) and 1×200 ml water
3. dry with materialThe organic layer was dried over magnesium sulphate
4. filtrationfiltered
5. customAfter the evaporation of the solvent the oily raw product
6. distillationpurified by vacuum distillation (63° C./0.032 mbar)

ORD record

ord-f01e751ba0d340ed8c9bd2314a99aca3

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198388B2