반응식
[CH3:1][C:2]1[CH:7](/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11])[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=1.[Mg].[CH:16](Br)=C>O1CCCC1>[CH3:16][CH:5]1[C:6]([CH3:14])([CH3:13])[CH:7](/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11])[C:2]([CH3:1])=[CH:3][CH2:4]1참가 물질
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- 온도
- 0 °C
실험 절차
A solution of 50 g (0.26 mol) of α-ionone in 150 ml of tetrahydrofuran was allowed to drop over a period of 20 minutes into a Grignard solution, which was cooled to 0° C. and which had been prepared from 9.72 g (0.4 mol) of magnesium shavings in 75 ml of tetrahydrofuran and 44.9 g (0.42 mol) of vinyl bromide in 180 ml of tetrahydrofuran, in such a manner that the temperature lay between 15° C. and 20° C. Subsequently, the mixture was stirred at room temperature for a further 3 hours and worked-up as described in Example 8. There were obtained 54.5 g of crude product which contained above 92% 9-vinyl-α-ionol according to GC and which was further processed directly in this form. In a manner analogous to the epoxidation of α-irone (Example 4), from 53.2 g (0.242 mol) of 9-vinyl-α-ionol there was obtained 59.0 g of crude 9-vinyl-α-ionol epoxide of which 58.0 g were dissolved together with 26.5 g (0.13 mol) of aluminium isopropylate in 175 ml of isopropanol. By following the procedure described in Example 1 there were obtained 57 g of a crude product. From this crude product there were obtained by distillation over a 20 cm Widmer column 15.0 g (26%) of olfactorily good product of boiling point 73°-74° C./0.3 mmHg which contained above 85% 20a and 20b in the approximate ratio of 3:2. In addition, there were present small amounts of the corresponding 7-oxa-bicyclooctane 20c. ##STR33##
후처리
- customlay between 15° C. and 20° C
- customThere were obtained 54.5 g of crude product which
출처 및 근거
- ORD 기록
- ord-a2de372ab39e49d38d2cd9a737d1bcaf
- 출처 데이터셋
- uspto-grants-1984_11
- 특허 번호
- US04485036
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