4'-Hydroxyacetophenone → 4'-(METHOXYMETHOXY)ACETOPHENONE

HRID 1402961Notes

Reaction equation

HRID 1402961 reaction equation
Br[CH2:2][O:3][CH3:4].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.[H-].[Na+]>O>[CH3:4][O:3][CH2:2][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 74694'-HydroxyacetophenoneHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl ether

Product 1

HCID 44249974'-(METHOXYMETHOXY)ACETOPHENONE

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromomethyl-methylether (0.87 ml) was added dropwise to a stirred suspension of p-hydroxyacetophenone (1 g) and sodium hydride (0.44 g) at 0° C. under nitrogen. The mixture was stirred for 1 h at room temperature. Then water was added and the mixture was extracted with ethylacetate. The organic layer was dried over magnesium sulphate and concentrated in vacuo to leave p-methoxymethoxyacetophenone (1.4 g) as yellow solid which was processed without further purification.

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32729ff6007843d3b3bd946fa21c43f4
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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