Water → 1-Isopropyl-4-(2-methyl-3-(4-methylphenoxy)propene-1-yl)benzene

HRID 2376298Notes

Reaction equation

HRID 2376298 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[H-].[Na+].Br[CH2:12][C:13]([CH3:24])=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=1.O>CN(C=O)C>[CH:21]([C:18]1[CH:17]=[CH:16][C:15]([CH:14]=[C:13]([CH3:24])[CH2:12][O:7][C:6]2[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=2)=[CH:20][CH:19]=1)([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 24758Sodium hydrideHCID 687079861-(3-Bromo-2-methyl-1-propenyl)-4-isopropylbenzene

Product 1

HCID 687104171-Isopropyl-4-(2-methyl-3-(4-methylphenoxy)propene-1-yl)benzeneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of p-cresol (3.50 g, 32.3 mmol) in DMF (70 mL) was added sodium hydride (a 60% liquid paraffin dispersion, 1.42 g, 35,5 mmol) under nitrogen atmosphere at 0° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(3-bromo-2-methyl-1-propenyl)-4-isopropyl benzene (9.0 g, 35.5 mmol), and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the product was extracted with diisopropyl ether. The extract was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 8.20 g (yield 91%) of the title compound. Oily matter.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe product was extracted with diisopropyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-cbd06352527a436dbf9b3285cb6ba02d
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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