Methyl iodide → Cyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone

HRID 2051405Notes

Reaction equation

HRID 2051405 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:5]([OH:19])=[C:6]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1.[CH3:20]I>CN(C)C=O>[CH3:3][C:4]1[C:5]([O:19][CH3:20])=[C:6]([C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15094963Cyclohexyl 3,5-dimethyl-2-hydroxyphenyl ketone

Product 1

HCID 15157169Cyclohexyl 3,5-dimethyl-2-methoxyphenyl ketoneYield 105%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

53 Grams of 60% sodium hydride was gradually added to a solution prepared by dissolving 256.2 g of cyclohexyl 3,5-dimethyl-2-hydroxyphenyl ketone in 1 liter of dimethylformamide with stirring, generating the temperature of the reaction mixture was risen to 70° C. by generating the heat. After continuation of stirring for 30 minutes, the reaction mixture was cooled to room temperature and thereto was added dropwise 233 g of methyl iodide. The reaction mixture was further stirred at the same temperature for 2 hours and then added to 1 liter of ice water and stirred. The organic layer was extracted with 3 liters of ethyl acetate. The extract was washed with water and then with a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 285.2 g of cyclohexyl 3,5-dimethyl-2-methoxyphenyl ketone.

Workup

  1. customprepared
  2. customwas risen to 70° C.
  3. stirringAfter continuation of stirring for 30 minutes
  4. stirringThe reaction mixture was further stirred at the same temperature for 2 hours
  5. stirringstirred
  6. extractionThe organic layer was extracted with 3 liters of ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialwith a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5bbc77fbfee0451fa7c2cece7073fd9b
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

Loading…