Toluene → HCID 86622669, compound

Participants

Reaction Steps

A solution of 5-isopropyl-7,7-dimethyl-bicyclo[3.2.1]octan-2-ol (18.5 g, 88 mmol) and KHSO4 (100 mg) in toluene (250 ml) was heated 36 h in a Dean-Stark apparatus. The solution was cooled and washed once with water and brine, dried (MgSO4) and concentrated in vacuo to yield 5-isopropyl-2,7,7-trimethyl-bicyclo[3.2.1]oct-2-ene (13.77 g, 81%). 13H-NMR (100 MHz, CDCl3): 140.4 (s), 118.7 (d), 52.1 (d), 51.5 (t), 46.1 (s), 46.0 (s), 39.1 (t), 37.6 (d), 37.4 (t), 31.5 (q), 26.9 (q), 24.6 (q), 18.2 (q), 18.0 (q) ppm. GC/MS (EI): 192 (M+, 17), 177 (4), 149 (22), 136 (21), 121 (15), 107 (18), 93 (100), 77 (28), 57 (17), 41 (23). IR (ATR): 2957 s, 2933 s, 2869 m, 1468 m, 1452 m, 1366 m cm−1.

Provenance & Evidence