2,3-Dimethylanisole → 2-Methoxy-6-methylbenzaldehyde

HRID 2036042Notes

Reaction equation

HRID 2036042 reaction equation
S1(OS(=O)(=O)OOOO1)(=O)=O.[K].[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[O:21][CH3:22].C(OCC)(=[O:25])C.CCCCCC>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]=1[CH:13]=[O:25]

Participants

6

Reactant 3

HCID 762692,3-DimethylanisoleHCID 21226206Ethyl acetate hexaneHCID 86652980Potassium peroxy disulphate

Product 1

HCID 6402382-Methoxy-6-methylbenzaldehydeYield 44.2%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Potassium peroxy disulphate (89.31 g, 0.33 mol) and copper (II) sulphate pentahydrate (27.22 g, 0.11 mol) was added to a solution of 2,3-dimethylanisole (15 g, 0.11 mol) in acetonitrile water mixture (750 ml, 1:1). The reaction mixture was stirred for 15 min at reflux until no starting material remained as judged by TLC (Thin Layer Chromatography). On cooling the reaction mixture to room temperature, the product was extracted into dichloromethane (2×225 ml). The organic layer was washed with water (2×100 ml) and brine solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product. Column chromatography using 4/96 ethyl acetate/hexane yielded 2-Methoxy-6-methylbenzaldehyde (7.32 g, 44.2%).

Workup

  1. temperatureat reflux until no starting material
  2. extractionthe product was extracted into dichloromethane (2×225 ml)
  3. washThe organic layer was washed with water (2×100 ml) and brine solution (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product

Sources & evidence

ORD record
ord-2d879bee0a704ed7b2f08809380094d4
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

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