Water → 2-O-Methylpyrogallol

HRID 1511229Notes

Reaction equation

HRID 1511229 reaction equation
[C:1](=O)([O-])[O-].[Li+].[Li+].[C:7]1([CH:15]=[CH:14][CH:13]=[C:11]([OH:12])[C:9]=1[OH:10])[OH:8].CI.O>CN(C)C=O>[CH3:1][O:10][C:9]1[C:7]([OH:8])=[CH:15][CH:14]=[CH:13][C:11]=1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1057PyrogallolHCID 6328Methyl iodideHCID 11125Lithium Carbonate

Product 1

HCID 1218052-O-MethylpyrogallolYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Lithium carbonate (281 mg, 1.98 mmol) was added to pyrogallol (100 mg, 0.79 mmol) in N,N-dimethylformamide (3.0 mL) at room temperature. After 5 minutes, methyl iodide (130 μL, 1.98 mmol) was added and the resulting solution was heated to 50° C. for 48 hours. Upon cooling to room temperature, water (20 mL) was added and the solution was extracted with EtOAc (3×20 mL). Combined organic fractions were dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 5:1→1:1 Hexane:EtOAc) to afford 19 as a colorless amorphous solid (44.2 mg, 34%): 1H NMR (CDCl3, 400 MHz) 6.89 (td, J=8.0, 0.9 Hz, H), 6.53 (dd, J=8.2, 0.8 Hz, 2H), 5.83 (bs, 2H), 3.90 (s, 3H).

Workup

  1. temperatureUpon cooling to room temperature
  2. extractionthe solution was extracted with EtOAc (3×20 mL)
  3. dry with materialCombined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via column chromatography (SiO2, 5:1→1:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-20cf0c88eab546b791b838de4a8b5c32
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

Loading…