Acetone → (2-Methoxy-5-methylphenyl)(phenyl)methanone

HRID 393998

Reaction equation

HRID 393998 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CI.[CH3:19]C(C)=O>O>[CH3:19][O:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6328Methyl iodideHCID 738512-Hydroxy-5-methylbenzophenone

Product 1

HCID 249273(2-Methoxy-5-methylphenyl)(phenyl)methanoneYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.00 g (23.5 mmole) 2-hydroxy-5-methyl-benzophenone and 6.67 g (47.1 mmole) methyliodide in 50 ml abs. acetone 4.50 g (32.6 mmole) potassium carbonate are added. The reaction mixture is then heated for 5 hours with recycling. Following cooling, 50 ml water and 50 ml petroleum ether (30/60) are added to the suspension. The organic phase is separated off, the aqueous phase is extracted twice with 75 ml petroleum ether (30/60) and the purified organic phase is washed twice with 50 ml 10% NaOH solution. The organic phase is then dried through magnesium sulphate and the solvent is removed. 3.80 g (16.8 mmole, 71%) 2-methoxy-5-methyl-benzophenone are obtained.

Workup

  1. temperatureThe reaction mixture is then heated for 5 hours
  2. temperatureFollowing cooling
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted twice with 75 ml petroleum ether (30/60)
  5. washthe purified organic phase is washed twice with 50 ml 10% NaOH solution
  6. dry with materialThe organic phase is then dried through magnesium sulphate
  7. customthe solvent is removed

Sources & evidence

ORD record
ord-e73b8a03b84542dca98e32e08bdf1543
Source dataset
uspto-grants-2004_10
Patent number
US06809225B2

Linked notes

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