Water → 2-Bromo-4-ethoxymethoxy-1-methylbenzene

HRID 584285Notes

Reaction equation

HRID 584285 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[H-].[Na+].[CH3:12][O:13][CH2:14][CH2:15]Cl.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:12][O:13][CH2:14][CH3:15])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 103079133-Bromo-4-methylphenol

Product 1

HCID 223455862-Bromo-4-ethoxymethoxy-1-methylbenzeneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.1 g (65 mmol) of 3-bromo-4-methylphenol are placed in 100 ml of dry dimethylformamide in a round-bottomed flask and under a stream of nitrogen. At 0° C., 3.1 g (78 mmol) of 60% sodium hydride are added slowly. After 1 hour, 7.3 ml (78 mmol) of methoxyethyl chloride are added dropwise. The mixture is stirred at room temperature overnight. It is then poured into water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (85/15) to give 13.2 g (83%) of the expected product in the form of an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (85/15)

Sources & evidence

ORD record
ord-82487739fae04980951c68a35d6243d8
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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