(1,4-Dimethoxynaphthalen-3-yl)methanol → 1,4-Dimethoxy-2-naphthaldehyde

HRID 1742497Notes

Reaction equation

HRID 1742497 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][OH:16]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH:15]=[O:16]

Participants

4

Reactant 1

HCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanol

Product 1

HCID 105848151,4-Dimethoxy-2-naphthaldehydeYield 66.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4.18 g of manganese dioxide were added to a solution of 0.87 g of 1,4-dimethoxy-2-naphthylmethanol (prepared as described in Preparation 20) in 10 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 6.5 hours. At the end of this time, the reaction mixture was filtered to remove inorganic materials, and the filtrate was dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting crystalline residue was washed with hexane and air-dried, to give 0.57 g of the title compound as pale yellow needles, melting at 120°-123° C.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove inorganic materials
  3. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. washThe resulting crystalline residue was washed with hexane
  6. customair-dried

Sources & evidence

ORD record
ord-017f95443a7743c6b8f816864100c579
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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