Methyl iodide → 1-(2-Hydroxy-4-methoxy-phenyl)-2-methyl-propan-1-one

HRID 493188Notes

Reaction equation

HRID 493188 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:13])[CH:10]([CH3:12])[CH3:11].IC.[C:16]([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:16])[CH:5]=[CH:4][C:3]=1[C:9](=[O:13])[CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 159157311-(2,4-Dihydroxyphenyl)-2-methylpropan-1-one

Product 1

HCID 687238621-(2-Hydroxy-4-methoxy-phenyl)-2-methyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above prepared 1-(2,4-dihydroxy-phenyl)-2-methyl-propan-1-one (1.13 g, 5.55 mmol, corrected for purity) was dissolved in 22 mL of acetonitrile and treated successively at 0° C. with iodomethane (0.36 mL, 1.05 eq.) and Cs2CO3 (1.998 g, 1.1 eq.), and the mixture then stirred over night at ambient temperature. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=95/5), delivered 0.740 g of the title compound as colorless oil.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7e46fa0d283c44ef827412d5e7d16e22
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

Loading…