2-Hydroxymethyl-5,6,7-trimethoxynaphthalene → 5,6,7-Trimethoxynaphthalene-2-carbaldehyde

HRID 720309Notes

Reaction equation

HRID 720309 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:17][CH3:18])=[C:8]([O:15][CH3:16])[C:9]=2[O:13][CH3:14])[CH:4]=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O>ClCCl>[CH3:14][O:13][C:9]1[C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([CH:2]=[O:1])=[CH:4]2

Participants

4

Reactant 2

HCID 218915782-Hydroxymethyl-5,6,7-trimethoxynaphthaleneHCID 86587493Pyridium dichromate

Product 1

HCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Hydroxymethyl-5,6,7-trimethoxynaphthalene (3.78 g) was dissolved in dichloromethane (100 mL), pyridium dichromate (8.61 g) was added to the solution, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered, and insoluble matter was fully washed with chloroform. After the washings were combined with the filtrate and concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and the solution was successively washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3 to 1:1) and further recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washinsoluble matter was fully washed with chloroform
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe solution was successively washed with 2 M hydrochloric acid, water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3 to 1:1)
  9. customfurther recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b5caa6d911924c8d8f6d492a9355dfa7
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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