4-Bromotoluene → 4,4',4''-Trimethyltrityl alcohol

HRID 80313

Reaction equation

HRID 80313 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH3:10][C:11]1[CH:25]=[CH:24][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([C:3]2[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=2)([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[OH:16])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 78054-BromotolueneHCID 691484,4'-DimethylbenzophenoneHCID 516892Sodium BicarbonateHCID 5462224Magnesium

Product 1

HCID 767334,4',4''-Trimethyltrityl alcoholYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A Grignard reagent was prepared from magnesium (0.14 g, 5.76 mmol) (Wako Pure Chemical Industries, Ltd.) and p-bromotoluene (0.48 g, 5.45 mmol) (Wako Pure Chemical Industries, Ltd.). 4,4′-dimethylbenzophenone (0.60 g, 2.85 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in tetrahydrofuran (5 mL) (KANTO CHEMICAL CO., INC.), and it was added dropwise to the Grignard reagent while cooling with ice, followed by stirring at room temperature for 4 hours. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution while cooling with ice, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was washed with brine. After that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.):ethyl acetate (Wako Pure Chemical Industries, Ltd.)=19:1 as an eluent), to thereby obtain the title compound (0.74 g, 86% yield).

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice, and mixture
  3. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  4. washThe organic layer was washed with brine
  5. dry with materialAfter that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5df918343d3e4682a4c2f060ed77f6dd
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Linked notes

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