Chloromethyl Methyl Ether → 1-[2-(Methoxymethoxy)phenyl]ethan-1-one

HRID 475557Notes

Reaction equation

HRID 475557 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH3:11][O:12][CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][O:12][CH2:13][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 102616991-[2-(Methoxymethoxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A 10 g quantity of 1-(2-hydroxyphenyl)ethanone was dissolved in 100 ml of dimethylformamide, and 11.2 ml of chloromethyl methyl ether and 25.4 g of potassium carbonate were added. The mixture was stirred at 50° C. for 6 hours and then at room temperature for 4 days. After insolubles were removed from the reaction mixture by filtration, ice water was added to the filtrate and extraction with ethyl acetate was performed. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give 6.26 g of colorless oily 1-(2-methoxymethoxyphenyl)ethanone.

Workup

  1. waitat room temperature for 4 days
  2. customAfter insolubles were removed from the reaction mixture by filtration, ice water
  3. additionwas added to the filtrate and extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ca185990bbda456184b08f6c1cf5d7e1
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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