Methyl iodide → alpha-Irone

HRID 1413355

Reaction equation

HRID 1413355 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 5371002alpha-Irone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent5×

Conditions

Temperature
0 °C

Procedure

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 (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 was obtained 68.0 g of crude 9-methyl-α-ionol epoxide.

Workup

  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

Sources & evidence

ORD record
ord-a8f55ca780984ef7a139bace122ef264
Source dataset
uspto-grants-1981_02
Patent number
US04250099

Linked notes

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