4,4'-Dimethoxybenzophenone → α-Ethyl-4-methoxy-α-(4-methoxyphenyl)benzenemethanol

HRID 1282466Notes

Reaction equation

[CH2:1]([Mg]Cl)[CH3:2].[CH3:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1.[Cl-].[NH4+]>C1COCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:22][CH:21]=2)([OH:12])[CH2:1][CH3:2])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 4 °C

Procedure

Into a reactor were introduced 31.9 mL (30.9 mol; 0.97 M THF solution) of ethylmagnesium chloride and 20 mL of THF under a nitrogen atmosphere. The contents were cooled to 4° C. Thereafter, a solution prepared by mixing 5.00 g (20.6 mmol) of 4,4′-dimethoxybenzophenone with 20 mL of THF was gradually added dropwise thereto, and this mixture was stirred at room temperature for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction mixture. The organic layer was extracted with ethyl acetate, and the extract was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 3.06 g (55%) of the target compound as a light-yellow oily substance.

Workup

customThereafter, a solution prepared
additionwas gradually added dropwise
extractionThe organic layer was extracted with ethyl acetate
dry with materialthe extract was dried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate was purified by column chromatography

Sources & evidence

ORD record: ord-441547c40cd34fb49b9541a13f2d3b53
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455720B1

Reaction notes

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