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

HRID 1282466
Notes
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Reaction equation

HRID 1282466 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 70324,4'-DimethoxybenzophenoneHCID 25517Ammonium ChlorideHCID 178461633HCID 178461633, compound

Product 1

HCID 18424508α-Ethyl-4-methoxy-α-(4-methoxyphenyl)benzenemethanolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customThereafter, a solution prepared
  2. additionwas gradually added dropwise
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialthe extract was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes