100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere; |
1 Production of 3,7-Dimethyl-6-Octenyl-9-Decenoate
In a 100mL flask, 3,7-dimethyl-6-octene-1-ol ((6)-citronellol, manufactured by Wako Pure Chemical Industries,Ltd., Purity: 90%, 2.1g, 12.1 mmol) and 9-decenoic acid (2.4 g, 14.0 mmol) were placed and then were dissolved indichloromethane (25 mL). Subsequently, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.2 g, 16.5mmol, 136 mol% with respect to 3,7-dimethyl-6-octene-1-ol and 118 mol% with respect to 9-decenoic acid) and N,N’-dimethylaminopyridine (146 mg, 1.2 mmol, 10 mol% with respect to citronellol) were added to the flask.This was allowed to react under a nitrogen gas stream at room temperature for five hours. An ammoniumchloride aqueous solution was added to a reaction solution obtained after the reaction was completed, which then wasstirred. Thereafter, it was subjected to settled separation and thereby an aqueous layer was extracted and an oil layerwas washed with saturated saline. Then sodium sulfate was added to the oil layer to dehydrate to dryness. After filtrationthereof, dichloromethane was evaporated to dryness from the oil layer and thereby 3,7-dimethyl-6-octenyl-9-decenoate(3.7 g, 12.0 mmol, the yield in terms of 3,7-dimethyl-6-octene-1-ol: 100%) was obtained.[0107] The measurement results of respective spectrum analyses of 3,7-dimethyl-6-octenyl-9-decenoate are shownbelow.(1) 1H-NMR (CDCl3, 400 MHz); δ (ppm): 0.91 (d, 3H, J=6.4 Hz), 1.18 (m, 1H), 1.30-1.47 (m, 10H), 1.50-1.70 (m,4H), 1.60 (s, 3H), 1.68 (s, 3H), 1.92-2.05 (m, 4H), 2.28 (t, 2H, J=7.6 Hz), 4.09 (m, 2H), 4.92 (d, 1H, J=10.0 Hz), 4.98(d, 1H, J=17.2 Hz), 5.08 (t, 1H, J=7.0 Hz), 5.79 (m, 1H).(2) 13C-NMR (CDCl3, 100 MHz); δ (ppm): 174.1, 139.3, 131.5, 124.8, 114.4, 63.1, 37.4, 35.9, 34.8, 34.2, 29.9, 29.5,29.5, 29.4, 29.3, 26.2, 25.8, 25.4, 19.9, 18.1.(3)MS(CI) m/Z: 309(M+), 171, 139, 83, 71 |