Isopropanol → HCID 86709872, compound

Participants

Reaction Conditions

Reaction Steps

To a 125 mL 3-neck round bottom flask fitted with a condenser, nitrogen inlet, overhead stirrer, thermometer and heating mantle was charged isopropyl 4,5-dichloro-6-(4-chlorophenyl)picolinate (7.6 g, 22.1 mmol) and isopropyl alcohol (70 mL). Reaction mixture was heated to 40° C. and potassium hydroxide (85%, 5.1 g, 77.4 mmol) and water (5 mL) were added. Solids precipitated from the mixture, and it became difficult to stir. The mixture was diluted with water (250 mL) to dissolve most of the solids and allowed to stir at room temperature. Concentrated HCl (12 N, 5.6 mL) was added dropwise to the reaction mixture to achieve a pH of ˜2 and solids precipitated from the mixture. The solids were isolated by vacuum filtration and washed with water (2×100 mL), then allowed to dry to give 7.3 g (108% yield by weight) of 4,5-dichloro-6-(4-chlorophenyl)picolinic acid as a white solid. 1H NMR (400 MHz, THF-d8/D2O) δ 8.19 (d, J=11.2 Hz, 1H), 7.84-7.73 (m, 2H), 7.50 (dd, J=10.3, 3.5 Hz, 2H); 13C NMR (101 MHz, THF-d8/D2O) δ 167.70, 156.03, 152.40, 143.60, 136.49, 134.76, 131.22, 129.24, 128.04, 124.71; mp=229° C.

Provenance & Evidence