Chloromethyl Methyl Ether → 2-(Methoxymethoxy)-1-phenylethanone

HRID 883118Notes

Reaction equation

HRID 883118 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[H-].[Li+].[CH2:13](Cl)[O:14][CH3:15].[NH4+].[Cl-]>CN(C=O)C>[CH3:13][O:14][CH2:15][O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 25517Ammonium ChlorideHCID 62714Lithium hydrideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 105115712-(Methoxymethoxy)-1-phenylethanoneYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 2-hydroxyacetophenone (1.0 g, 7.3 mmol) in DMF (50 mL) was added lithium hydride (74 mg, 95%, 8.8 mmol). After stirring for 30 minutes, MOM-Cl (0.73 mL, 9.5 mmol) was added slowly via syringe and the mixture was allowed to warm slowly to room temperature and was stirred for 16 hours. The reaction mixture was treated with saturated NH4Cl (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (6×50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The brown residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate) to provide the product as a colorless oil (0.60 g, 45%).

Workup

  1. stirringwas stirred for 16 hours
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with water (6×50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe brown residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-58c8aa4658a6488394aaae72c336f271
Source dataset
uspto-grants-2012_08
Patent number
US08236825B2

Reaction notes

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