Hydrochloric Acid → 1,2-Bis(4-methylphenyl)ethan-1-one

HRID 1271263Notes

Reaction equation

HRID 1271263 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][Mg]Cl)=[CH:17][CH:16]=1.Cl>O1CCCC1.O>[C:9]1([CH3:12])[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:14][C:15]2[CH:23]=[CH:22][C:18]([CH3:19])=[CH:17][CH:16]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5133773N-Methoxy-N,4-dimethylbenzamideHCID 178425359HCID 178425359, compound

Product 1

HCID 125039001,2-Bis(4-methylphenyl)ethan-1-oneYield 64.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of 10.40 g of N-methoxy-N-methyl-p-toluamide in 100 ml of tetrahydrofuran was ice-cooled and 4-methylbenzylmagnesium chloride (solution prepared by dissolving 10.60 g of α-chloro-p-xylene and 1.94 g of magnesium in 85 ml of tetrahydrofuran) was added dropwise. After stirring for one hour, 100 ml of 10% hydrochloric acid was slowly added. The reaction solution was diluted with water, extracted with diethyl ether, washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the crude crystal was washed with diisopropyl ether and then dried under reduced pressure to obtain 8.43 g of the desired compound as a colorless crystal having a melting point of 93 to 100° C.

Workup

  1. temperaturecooled
  2. extractionextracted with diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe crude crystal was washed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-da645eb9e0324749b0b8bb79768544e9
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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