Ethyl 3,3-dimethyloxirane-2-carboxylate → 3-Butenoic acid, 2-hydroxy-3-methyl-, ethyl ester

Temperature

81 °C

Tosic acid monohydrate (0.132 g, 0.694 mmol) was dehydrated by aezotropic destillation with benzene (3×10 ml) in a rotary evaporator flushed with nitrogen. Thereafter benzene (100 ml) and ethyl 3,3-dimethyloxirane-2-carboxylate (1 g, 6.94 mmol) were added and the resulting mixture was stirred at reflux (81° C.) overnight. The clear reaction mixture was then cooled to room temperature, cooled to 4° C. for a couple of hours, and then filtered over a glass filter to remove the crystallized tosic acid. The filtrate was concentrated in vacuo (40° C., 50 mbar) to yield 778 mg of crude product (containing 2.5 wt % benzene) which was used without further purification in the next step.

1. customflushed with nitrogen
2. temperatureThe clear reaction mixture was then cooled to room temperature
3. temperaturecooled to 4° C. for a couple of hours
4. filtrationfiltered over a glass
5. filtrationfilter
6. customto remove the crystallized tosic acid
7. concentrationThe filtrate was concentrated in vacuo (40° C., 50 mbar)

ORD record

ord-9ed825ffe578499d8614486e5f7377cb

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08669208B2