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

HRID 2051406Notes

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

Conditions

Temperature: 70 °C

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 heat at 70° C. 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

customprepared
stirringAfter continuation of stirring for 30 minutes
temperaturethe reaction mixture was cooled to room temperature
stirringThe reaction mixture was further stirred at the same temperature for 2 hours
stirringstirred
extractionThe organic layer was extracted with 3 liters of ethyl acetate
washThe extract was washed with water
dry with materialwith a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-dc72f1737d884503beb9cc9815735e4a
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05017724

Reaction notes

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