1-Hydroxymethyl-7-Methoxynaphthalene → 7-Methoxy-1-naphthaldehyde

HRID 1370768Notes

Reaction equation

HRID 1370768 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][OH:14])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[Mn+2]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH:13]=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 154530791-Hydroxymethyl-7-Methoxynaphthalene

Product 1

HCID 157882797-Methoxy-1-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

19.2 g (0.1 mol) of the compound obtained in Step B are dissolved in 300 ml of CH2Cl2. Under argon, 65 g (7.5 eq) of manganese oxide are added in three stages (t═0: 25 g, t=3 h :25 g, and t=24 h: 15 g). The alcohol is totally oxidised after a further 24 hours. The mixture is then filtered over Celite in order to remove the mineral compounds, rinsed with CH2Cl2 and then filtered over silica to yield an oil which solidifies on cooling.

Workup

  1. filtrationThe mixture is then filtered over Celite in order
  2. customto remove the mineral compounds
  3. washrinsed with CH2Cl2
  4. filtrationfiltered over silica
  5. customto yield an oil which
  6. temperatureon cooling

Sources & evidence

ORD record
ord-467bf61754434fb3864e7c0cd839ca9c
Source dataset
uspto-grants-2003_06
Patent number
US06583319B1

Reaction notes

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