Toluene → 5,8-Dimethyl-2-naphthaldehyde

HRID 278039Notes

Reaction equation

HRID 278039 reaction equation
ClC1[C:7](=[O:8])[C:6]([C:9]#N)=[C:5](C#N)[C:4](=O)C=1Cl.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCOC[CH2:23]1>>[CH3:21][C:15]1[CH:20]=[CH:19][C:18]([CH3:23])=[C:17]2[C:16]=1[CH:4]=[CH:5][C:6]([CH:7]=[O:8])=[CH:9]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-Dioxane

Product 1

HCID 144876095,8-Dimethyl-2-naphthaldehyde

Procedure

Under nitrogen atmosphere, 20.9 g of this crude aldehyde was dissolved in 300 ml of dioxane, followed by the addition of 50.9 g of dichlorodicyanobenzo-quinone. The resulting mixture was heated under reflux for 1.5 hours and cooled to room temperature by allowing to stand. Then, 500 ml of toluene was added to the resulting mixture to thereby form a precipitate. The resulting precipitate-containing mixture was filtered and the filter cake was washed with toluene several times. The filtrate was concentrated and the resulting crude product was purified by silica gel column chromatography to give 10.3 g of the title compound as colorless crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customto thereby form a precipitate
  4. additionThe resulting precipitate-containing mixture
  5. filtrationwas filtered
  6. washthe filter cake was washed with toluene several times
  7. concentrationThe filtrate was concentrated
  8. customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a4533d2f441461eb30254da33fee959
Source dataset
uspto-grants-2002_03
Patent number
US06358995B1

Reaction notes

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