3-Chloro-2-methyl-1-propene → HCID 334095, compound

HRID 1610762Notes

Reaction equation

HRID 1610762 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Cl)[C:17](=[CH2:19])[CH3:18]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[O:8][CH2:18][C:17]([CH3:19])=[CH2:16]

Participants

6

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 231092-Bromo-4-methylphenol

Product 1

HCID 334095HCID 334095, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-p-cresol (10 ml, 82.7 mmol) in N,N-dimethylformamide (200 ml) were added potassium carbonate (17.2 g, 124 mmol) and methallyl chloride (9.8 ml, 99.2 mmol), and the mixture was stirred at 100° C. overnight. The mixture was diluted with ethyl acetate, and washed with water and saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 2-bromo-4-methyl-1-[(2-methyl-2-propenyl)oxy]benzene (19.67 g, 99%) as a colorless transparent oil.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-345d97f6946146b3bbbc6dee738d4065
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…