Chloromethyl Methyl Ether → HCID 10988982, compound

HRID 565673Notes

Reaction equation

HRID 565673 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[OH:11].[H-].[Na+].[CH3:14][O:15][CH2:16]Cl>CN(C)C=O.O>[Br:1][C:2]1[C:3]([O:11][CH2:14][O:15][CH3:16])=[C:4]([CH3:10])[C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 22110976HCID 22110976, compound

Product 1

HCID 10988982HCID 10988982, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Under nitrogen gas, a solution of 2-bromo-3,5,6-trimethylphenol (10 g) in N,N-dimethylformamide (50 mL) was added dropwise to a suspension of 60% sodium hydride (2.1 g) in N,N-dimethylformamide (20 mL) under ice-cooling and the mixture was stirred for 10 minutes. To this mixture was further added a solution of chloromethyl methyl ether (3.9 mL) in N,N-dimethylformamide (5mL) dropwise and the mixture was stirred for another 30 minutes. This reaction mixture was diluted with iced water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3) to provide the title compound (12 g). Yield 99%.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for another 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3)

Sources & evidence

ORD record
ord-90b2c30da88746ab85001bb2c7fe9124
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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