Thionyl Chloride → HCID 9893279, compound

Participants

Reaction Steps

Thionyl chloride (15 mL) was added with stirring to the cis acid 12h (1.2 g, 2.2 mmol). The result was an orange mixture that became dark red within 15 min. After 6 h, the reaction mixture was diluted with benzene (25 mL) and evaporated to dryness. Chloroform (7 mL) was added to the purple solid and the solid was collected and washed with ether to give a light purple solid (0.75 g, 64%): mp 238-240° C.; IR (thin film) 3027, 2963, 1685, 1649, 1493, 1458, 1252, 1203, 1088, 1014 cm−1; 1H NMR (CDCl3, 300 MHz) δ7.96 (s, 1H), 7.62 (s, 1H), 7.38 (m, 1H), 7.21 (s, 1H), 7.11 (s, 1H), 5.23 (d, 4H, J=5.2 Hz), 4.02 (s, 3H) 3.95 (s, 3H), 3.81 (s, 3H); CIMS m/z (relative intensity) 534 (MH+, 22). Anal. Calcd for C33H27NO6: C, H, N.

Provenance & Evidence