Hydrochloric Acid → 4'-(METHOXYMETHOXY)ACETOPHENONE

HRID 2227501Notes

Reaction equation

HRID 2227501 reaction equation
[CH3:1][O:2][CH2:3]Cl.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.Cl>C(N(C(C)C)CC)(C)C>[CH3:1][O:2][CH2:3][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74694'-HydroxyacetophenoneHCID 7864Chloromethyl Methyl Ether

Product 1

HCID 44249974'-(METHOXYMETHOXY)ACETOPHENONEYield 93%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

4 ml of chloromethyl methyl ether was added dropwise to a solution of 4′-hydroxyacetophenone (5.44 g) and diisopropylethylamine (10 ml) in 40 ml dinethylformamide at room temperature and stirred at room temperature for 3 hours. After addition of 2 mol/l hydrochloric acid, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give a residue, which was then purified via column chromatography on silica gel (hexane:ethyl acetate=7:1) to provide 4′-(methoxymethoxy)acetophenone (6.73 g, 93%) as a colorless oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was evaporated
  6. customto give a residue, which
  7. customwas then purified via column chromatography on silica gel (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-e8b488ac94fd435fb568f249122ebe24
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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