Toluene → 5,8-Dimethyl-2-naphthaldehyde

HRID 1384068Notes

Reaction equation

HRID 1384068 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

In a nitrogen atmosphere, the obtained aldehyde (20.9 g) was dissolved in dioxane (300 ml). After adding dichlorodicyanobenzoquinone (50.9 g), the resultant mixture was heated under ref lux for 1.5 hr. Then, it was cooled to room temperature by allowing to stand followed by the addition of toluene (500 ml). The resulting precipitate was collected by filtration and washed with toluene several times. The filtrate was concentrated and the resulting crude product was purified by silica gel column chromatography to give 5,8-dimethyl-2-naphtaldehyde (10.3 g) as colorless crystals.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with toluene several times
  3. concentrationThe filtrate was concentrated
  4. customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6294218e16c246ea8157c401ff11b926
Source dataset
uspto-grants-2001_07
Patent number
US06258811B1

Reaction notes

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