2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Hydroxy-5-methoxy-8-fluoro-2-naphthaldehyde

HRID 374660Notes

Reaction equation

HRID 374660 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]2[C:11]=1[C:10](=[O:12])[CH:9]([CH:13]=[O:14])[CH2:8][CH2:7]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[OH:12][C:10]1[C:11]2[C:6](=[C:5]([O:15][CH3:16])[CH:4]=[CH:3][C:2]=2[F:1])[CH:7]=[CH:8][C:9]=1[CH:13]=[O:14]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 189969618-Fluoro-2-formyl-5-methoxytetralone

Product 1

HCID 104434321-Hydroxy-5-methoxy-8-fluoro-2-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8-Fluoro-2-formyl-5-methoxy-1-tetralone (20 g) was dissolved in dioxan. 2,3-Dichloro-5,6-dicyanobenzoquinone (21 g) was added and the mixture was heated under reflux for 2 hours. The mixture was allowed to cool and was filtered to remove solids. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate. The product solution was washed with saturated NaHCO3 (aq) (×3), dried (MgSO4), filtered and evaporated to give a dark solid. This material was recrystallised from ethyl acetate/hexane to give 1-hydroxy-5-methoxy-8-fluoro-2-naphthaldehyde, m.p. 156°-158° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. filtrationwas filtered
  5. customto remove solids
  6. customThe solvent was removed under reduced pressure
  7. washThe product solution was washed with saturated NaHCO3 (aq) (×3)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give a dark solid
  12. customThis material was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1f37db10a2404eab8bd068a2dea3068e
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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