Pyridine → HCID 19818995, compound

Participants

Reaction Steps

2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-oyl chloride was prepared from 2,2-bis(trifluoromethyl)-4-carboxy-1,3-dioxolane (see U.S. patent application 07/401,668, filed Aug. 30, 1989) (25.4 g, 0.1 mole). To this substrate was added pyridine (3.16 g, 0.04 mole) followed by thionyl chloride (14.3 g, 0.12 mole), with external cooling to maintain the pot at ambient temperature. When the addition was complete, the reaction mixture was heated slowly to 70° C. for 1.5 hour, then at 90° to 100° C. for 0.5 hour. The product was distilled from the reaction mixture, a clear colorless liquid, 22.0 g (81% yield) was obtained. Bp. 50° C./10 mm. 1H-NMR (Neat): δ 5.23 (t, J=7.0 Hz, 1H), 4.73 (m, 2H); 19F NMR (neat): -80.5 (q, J=8.5 Hz, 3F), -81.5 (q, J=8.5 Hz, 3F). Anal. Calc. for C6H3ClF6O3 : C: 26.44, H: 1.11, F: 41.83, Cl: 13.00; Found: C: 26.13, H: 1.11, F: 41.44, Cl: 13.38. ##STR6##

Provenance & Evidence