Dibromomethane → HCID 67160199, compound

Participants

Reaction Steps

Prepared as described in Example 10 from Terpinen-4-ol (2 g, 13 mmol) and dibromomethane (9.15 g, 52 mmol) in diethyl ether by dropwise addition of tent-butyl magnesium chloride 2M in diethyl ether (26 ml, 52 mmol) at 10°-20° C. Work-up after 16 h at 25° C. and bulb-to-bulb distillation gave 2.1 g (85%) of a colorless oil. Odour: Agrestic. 1H-NMR (CDCl3): δ 0.3 (dd, 1H), 0.43 (dd, 1H), 0.6 (dddd, 1H), 0.89 (d, 3H), 0.91 (d, 3H), 1.03 (s, 3H), 1.1-1.2 (m, 2H), 1.2-1.3 (m, 1H), 1.5-1.7 (2 m, 2H), 1.75-1.9 (2H), 2.2 (m, 2H) ppm. 13C-NMR: δ 14.4 (s), 16.2 (q), 16.4 (q), 17.7 (d), 19.9 (t), 27.2 (q), 28.1 (t), 31.6 (t), 31.9 (d), 35.7 (t), 72.8 (s). syn-configuration confirmed by COSY, HSQC, HMBC, NOESY in CDCl3. MS (EI): m/z (%) 168 [M]+, 3), 150 ([M-18]+, 8), 125 (32), 107 (65), 86 (38), 71 (80), 43 (100). IR (film): 3419 (br), 2936 (m), 2863 (m), 1458 (m), 1379 (w), 1302 (w), 1225 (w), 1133 (m), 1049 (w), 992 (s), 957 (w), 906 (w), 863 (w).

Provenance & Evidence