Sodium Methoxide → HCID 67955922, compound

HRID 1619177Notes

Reaction equation

HRID 1619177 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:6]=1[CH3:13])=[O:4].[CH3:14][O-:15].[Na+]>CO>[OH:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([C:3](=[O:4])[CH2:2][O:15][CH3:14])=[C:6]([CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86043019HCID 86043019, compound

Product 1

HCID 67955922HCID 67955922, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 mL of methanol, 0.4 g (2.0 mmol) 2-chloro-1-(4-hydroxy-2,5-dimethylphenyl)ethanone was reacted with 0.40 g (7.55 mmol) sodium methoxide at room temperature for 5 hours with stirring, and the solvent was removed at a reduced pressure. To the residue was added 20 mL of water, followed by adjusting the pH to 7 with conc. HCl. The aqueous layer was extracted twice with 3 mL of dichloromethane and the organic layer was dried over anhydrous magnesium sulfate and concentrated at a reduced pressure to afford a yellowish solid compound 1-(4-hydroxy-2,5-dimethylphenyl)-2-methoxyethanone (0.30 g, yield: 78%).

Workup

  1. customthe solvent was removed at a reduced pressure
  2. additionTo the residue was added 20 mL of water
  3. extractionThe aqueous layer was extracted twice with 3 mL of dichloromethane
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated at a reduced pressure

Sources & evidence

ORD record
ord-0c29ad05151740c890904a5c2ccdb4fa
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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