Methanol → HCID 73102453, compound

To a solution of 3-chloro-4,4-dimethylpent-2-enoic acid (0.8 g, 4.92 mmol) in methanol (20 mL) was added thionyl chloride (0.714 mL, 9.846 mmol) drop wise under stirring at ice cold temperature. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The solution was extracted with chloroform (3×100 mL) and the combined organic layer was washed with water, brine, dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (95:5) as eluents to give the product as a pale green color oil (750 mg, 87%). 1H NMR (400 MHz, CDCl3): δ 6.08 (1H, s), 3.75 (3H, s), 1.24 (9H, s).

1. temperatureThe reaction mixture was refluxed for 2 h
2. customattained to rt
3. additionThe mixture was poured into ice
4. stirringstirred for 15 min
5. extractionThe solution was extracted with chloroform (3×100 mL)
6. washthe combined organic layer was washed with water, brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customSolvent was evaporated
10. customthe residue was chromatographed over silica gel column

ORD record

ord-19b0154d964c4195a440a448a4ea70f6

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815879B2