Methanol → Methyl 2-methyl-2-pentenoate

Temperature

20 °C

A mixture of 2-methylpent-2-enoic acid (5.0 g, 44 mmol) and sulfuric acid (0.5 mL) in methanol (250 mL) was heated at reflux for 16 hours. The solution was allowed to cool down to 20° C. and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), distilled water (50 mL), then with brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give the title compound (5.1 g, 91%) as a colourless oil.

1. temperaturewas heated
2. temperatureat reflux for 16 hours
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
5. washwashed with saturated aqueous sodium hydrogen carbonate (2×50 mL)
6. distillationdistilled water (50 mL)
7. dry with materialThe organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-f10c196f927a4042b9075bfa57d32608

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2