2-(3-Furanyl)-4,6-dimethylphenol → 2,4-Dimethyl-6-(tetrahydro-3-furanyl)phenol

HRID 63387Notes

Reaction equation

HRID 63387 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=2[OH:14])=[CH:2]1>CO.[C].[Pd]>[CH3:13][C:8]1[CH:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[C:7]=1[OH:14]

Participants

4

Reactant 1

HCID 900027862-(3-Furanyl)-4,6-dimethylphenol2×

Product 1

HCID 900026252,4-Dimethyl-6-(tetrahydro-3-furanyl)phenolYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(furan-3-yl)-4,6-dimethylphenol (Compound 6-2) (0.6 g, 3.2 mmol) was dissolved in methanol. Palladium carbon (0.06 g) was added thereto, followed by stirring under hydrogen balloon at room temperature for 6 hours. After the completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and purified by column chromatography to obtain 2,4-dimethyl-6-(tetrahydrofuran-3-yl)phenol (0.45 g, 73%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-35ddfde00bc34636a37593b143daeb35
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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