19376-57-9

67-66-3

292638-85-8

19376-57-9

To a vigorously stirred aqueous solution (10 mL) of NaOH (10 g, 0.25 mol) was sequentially added BnEt3NCl (0.20 g, 0.878 mmol), methyl acrylate (4.0 mL, 44.4 mmol) and chloroform (40 g, 0.5 mol). The reaction mixture was stirred at 0 °C for 2 hours. After completion of the reaction, extraction was carried out by adding dichloromethane (50 mL) and water (50 mL), the organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by vacuum distillation to afford methyl 4,4,4-trichlorobutyrate (7.39 g, 36.0 mmol) as a colorless liquid in 81% yield. As an alternative purification method, the crude product can also be purified by rapid chromatography on silica gel using hexane/acetone (19:1) as eluent to give the target product. The boiling point of the product was 78 °C-80 °C/1 torr (literature boiling point 80 °C/0.3 torr).1H NMR (300 MHz, CDCl3) δ 3.72 (s, 3H), 2.95-3.13 (m, 2H), 2.68-2.86 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 171.6, 98.7, 52.3. 50.0, 31.4; no El- or ESI-MS signals were detected.