O-Xylene → HCID 22238068, compound

HRID 1743392Notes

Reaction equation

HRID 1743392 reaction equation
C[C:2]1C(C)=CC=[CH:4][C:3]=1[NH:9]CC(C)=C.[C:14]([O-])(=O)C.[Na+].[C:19]1([CH3:26])[C:20]([CH3:25])=[CH:21][CH:22]=[CH:23][CH:24]=1>O.[Cl-].[Zn+2].[Cl-]>[CH3:2][C:3]1([CH3:14])[CH2:4][C:23]2[C:24](=[C:19]([CH3:26])[C:20]([CH3:25])=[CH:21][CH:22]=2)[NH:9]1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 517045Sodium AcetateHCID 22238066HCID 22238066, compound

Product 1

HCID 22238068HCID 22238068, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,3-dimethyl-N-(2-methyl-2-propenyl)benzeneamine (3.77 g, 21.5 mmol) in xylene (35 mL) was added zinc chloride (8.80 g, 64.6 mmol), and the mixture was stirred at 150° C. for 3.5 hours. Heating was stopped, and a solution of sodium acetate (10.6 g, 0.129 mol) in water (30 mL) was carefully added dropwise to the resulting hot mixture. The resulting solution was cooled, the organic layer was separated, and the aqueous layer was extracted with toluene. The combined organic layers were washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 20:1) to obtain 2.91 g of the title compound.

Workup

  1. temperatureHeating
  2. temperatureThe resulting solution was cooled
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with toluene
  5. washThe combined organic layers were washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89867a3a0c404060a89d2beabefa8e1e
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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