Toluene → 5,8-Dimethyl-2-naphthaldehyde

HRID 277172Notes

Reaction equation

HRID 277172 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

20.9 g of the aldehyde compound was dissolved in 300 ml dioxane in a nitrogen atmosphere, then 50.9 g of dichlorodicyanobenzoquinone was added thereto, and the mixture was heated under reflux for 1.5 hours. After the mixture was left standing for cooling to room temperature, 500 ml toluene was added thereto, and the resulting precipitates were filtered off and 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 5,8-dimethyl-2-naphthaldehyde as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. waitAfter the mixture was left
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. washwashed 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-c4a762f1436d4ef49e4b284117a06862
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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