Thionyl Chloride → HCID 9826123, compound

Participants

Reaction Steps

Thionyl chloride (8.1 mL) was added with stirring to the cis acid 12g (0.7 g, 2.1 mmol). The result was a yellowish-brown mixture that became orange within 15 min and after 30 min was red. After 4 h, the reaction mixture was diluted with benzene (25 mL) and evaporated to dryness. The brownish-red solid was recrystallized from methanol and passed through a short column (SiO2), eluting with chloroform, to give a brown solid (0.14 g, 24%): MP 198-200° C.; 1H NMR (DMSO-d6) δ8.43 (d, J=8.0 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.75 (t, J=7.5 Hz, 1H), 7.39 (m, 13H), 5.34 (s, 1H), 5.29 (s, 1H), 3.93 (s, 1H); CIMS m/z (relative intensity) 474 (MH+, 100). Anal. Calcd for C31H23NO4: C, H, N.

Provenance & Evidence