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

HRID 2387601Notes

Reaction equation

HRID 2387601 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-hydroxy-1-phenylethanone (1.0 g, 7.3 mmol) in anhydrous DMF (50 mL) was added lithium hydride (74 mg, 95%, 8.8 mmol). After stirring the brown mixture for 30 minutes, MOM-Cl (0.73 mL, 9.5 mmol) was added slowly via syringe. The mixture warmed slowly to room temperature and stirred for 16 hours. The mixture was treated with NH4Cl (100 mL) and then extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (6×50 mL) and brine (50 mL) then 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 (0.60 g, 45%) as a colorless oil.

Workup

  1. stirringstirred 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 materialthen dried 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-3680b12153c74b5f994b1e0f7ba89a75
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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