3-Methylcatechol → 3-Methylveratrole

HRID 71052

Reaction equation

HRID 71052 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1O.[CH3:10]I.[C:12]([O-:15])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:10][O:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[C:3]=1[O:15][CH3:12]

Participants

5

Reactant 3

HCID 3403-MethylcatecholHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 782153-Methylveratrole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a round bottom flask, 3-methyl catechol (5.0 g, 40.3 mmol), MeI (22.3 g, 157.1 mmol), and K2CO3 (18.9 g, 136.9 mmol) were dissolved in acetone (20.0 ml). The reaction mixture was stirred at room temperature for 1 h, then at 60° C. for overnight. The reaction mixture was concentrated and chromatographed on silica gel using EtOAc/Hexane (5:95). A pale yellow liquid was isolated in 100% (6.13 g). The characterization of the compound matched previous report: Xing, L.; Wang, X.; Cheng, X.; Zhu, R.; Liu, B.; Hu, Y. Tetrahedron Letters 2007, 63, (38), 9382-9386.

Workup

  1. waitat 60° C. for overnight
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed on silica gel
  4. customA pale yellow liquid was isolated in 100% (6.13 g)

Sources & evidence

ORD record
ord-5680a16de7274cb5aacf4ba0058eddff
Source dataset
uspto-grants-2014_09
Patent number
US08822720B2

Linked notes

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