Methyl iodide → Paeonol

HRID 859644Notes

Reaction equation

HRID 859644 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:11]=1[C:17](=[O:19])[CH3:18]>CN(C=O)C>[CH3:1][O:16][C:14]1[CH:13]=[CH:12][C:11]([C:17](=[O:19])[CH3:18])=[C:10]([OH:9])[CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 69902',4'-DihydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 11092Paeonol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (27.2 g, 197 mmol) followed by methyl iodide (4.1 mL, 65.7 mmol) were added to a solution of 2′,4′-dihydroxyacetophenone (10.0 g, 65.7 mmol) in DMF (100 mL). The mixture was stirred for 4 hours and then partitioned between H2O and EtOAc. The organic layer was washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a clear oil (11.0 g). 1H NMR (300 MHz, CDCl3): δ 2.60- (s, 3 H), 3.80 (s, 3 H), 6.40 (s, 1 H) 6.51 (d, J=2.45 Hz, 1 H), 7.62 (d, J=8.67 Hz, 1 H), 12.90 (s, 1 H).

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with satd NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a clear oil (11.0 g)

Sources & evidence

ORD record
ord-591e877574fc4eaf851e85a16b167580
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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