Methanol → HCID 73102453, Verbindung

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).