Water → 1-Cyclobutyl-2-(methoxymethoxy)benzene

HRID 385045Notes

Reaction equation

HRID 385045 reaction equation
[CH:1]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:14][O:15][CH2:16]Cl.O>CN(C)C=O>[CH:1]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:11][CH2:14][O:15][CH3:16])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 128063072-Cyclobutylphenol

Product 1

HCID 681090621-Cyclobutyl-2-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-cyclobutylphenol (871 mg) was dissolved in N,N-dimethylformamide (5 mL), and 60% sodium hydride (1.30 g) was added to the solution at 0° C. After stirring the mixture for 30 minutes, chloromethyl methyl ether (2.1 mL) was added and the mixture was stirred for 14 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain the title compound (1.13 g) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred for 14 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6716d0dcbe154a4c90dd842f9a91bb64
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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