Methyl iodide → alpha-Irone

HRID 1980080

반응식

HRID 1980080 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].[CH3:16]I.[Cl-].[NH4+]>CCOCC>[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]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5282108Alpha-IononeHCID 5462224Magnesium

생성물 1

HCID 5371002alpha-Irone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매5회

반응 조건

온도
0 °C

실험 절차

A solution of 50.0 g (0.26 mol) of α-ionone in 150 ml of ether were 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 7.5 g (0.31 mol) of magnesium shavings in 75 ml of ether and 46.9 g (0.33 mol) of methyl iodide in 180 ml of ether, in such a manner that the temperature lay between 10° C. and 20° C. Subsequently, the mixture was stirred at the reflux temperature of the ether for a further 1 hour, cooled down to 0° C. and then cautiously treated with concentrated ammonium chloride solution and an additional 500 ml of ether. The ether phase was washed with water until neutral, dried and concentrated. There were obtained 60.0 g of crude product which contained above 95% 9-methyl-α-ionol (GC) and which was accordingly further processed directly in this form. In a manner analogous to the epoxidation of α-irone (Example 4), from 58.1 g (~0.26 mol) of 9-methyl-α-ionol there were obtained 68.0 g of crude 9-methyl-α-ionol epoxide.

후처리

  1. customlay between 10° C. and 20° C
  2. temperaturecooled down to 0° C.
  3. washThe ether phase was washed with water until neutral,
  4. customdried
  5. concentrationconcentrated
  6. customThere were obtained 60.0 g of crude product which

출처 및 근거

ORD 기록
ord-0b6e98d2b32e4431921c3570390d10e0
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04485036

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