2',4'-Dihydroxyacetophenone → 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone

HRID 1879552Notes

Reaction equation

HRID 1879552 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].Cl[CH2:19][O:20][CH3:21]>CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][O:20][CH3:21])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 117455591-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanoneYield 61.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 1-(2,4-dihydroxyphenyl)ethanone (1.52 g, 10 mmol) in 12 mL acetone was added K2CO3 (1.38 g, 10 mmol) followed by slow addition of chloro(methoxy)methane (885 mg, 11 mmol) with stirring under Ar atmosphere at rt. The reaction mixture was stirred at rt for 4 h and filtered. Solid was washed with EtOAc (80 mL) and the combined filtrate was washed with NaH2PO4 (sat. 50 mL) and water (80 mL) and dried over MgSO4 and concentrated. The crude product was purified with silica chromatography (hexane/EtOAc) to afford 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone as a off-white solid (1.2 g, 61%). MS (ESI) m/z 197 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at rt for 4 h
  2. filtrationfiltered
  3. washSolid was washed with EtOAc (80 mL)
  4. washthe combined filtrate was washed with NaH2PO4 (sat. 50 mL) and water (80 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified with silica chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-aba515d1a6f74cd1ba57b962ba9da9eb
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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