Pyrogallol → 2-O-Methylpyrogallol

HRID 2171119Notes

Reaction equation

HRID 2171119 reaction equation
[C:1]1([OH:9])[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[C:2]=1[OH:8].[C:10](=O)(O)[O-].[K+].CI>CC(C)=O>[CH3:10][O:8][C:2]1[C:3]([OH:7])=[CH:4][CH:5]=[CH:6][C:1]=1[OH:9]

Participants

5

Reactant 3

HCID 1057PyrogallolHCID 6328Methyl iodideHCID 516893Potassium Bicarbonate

Product 1

HCID 1218052-O-MethylpyrogallolYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring solution of benzene-1,2,3-triol (2 g, 15.87 mmol) in acetone was added potassium bicarbonate (1.9 g, 19.04 mmol) and methyl iodide (3.3 g, 23.8 mmol) and the resultant reaction mixture was heated to reflux for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The residue was diluted with ether, solid separated out was filtered and the filtrate was concentrated under reduced pressure to afford the crude product. The crude product was purified by flash column chromatography (silica gel, 0-15% ethyl acetate in pet ether) to afford 2-Methoxybenzene-1,3-diol as a solid (600 mg, 27%).

Workup

  1. customthe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 16 h
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe residue was diluted with ether, solid
  7. customseparated out
  8. filtrationwas filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto afford the crude product
  11. customThe crude product was purified by flash column chromatography (silica gel, 0-15% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-b20ce81e64024671848b6add10656bd0
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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