2-(2-Furanyl)-4,6-dimethylphenol → 2,4-Dimethyl-6-(tetrahydrofuran-2-yl)phenol

HRID 63390Notes

Reaction equation

HRID 63390 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[OH:14]>CO.[C].[Pd]>[CH3:13][C:8]1[CH:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[C:7]=1[OH:14]

Participants

4

Reactant 1

HCID 900027952-(2-Furanyl)-4,6-dimethylphenol2×

Product 1

HCID 900025812,4-Dimethyl-6-(tetrahydrofuran-2-yl)phenolYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(furan-2-yl)-4,6-dimethylphenol (Compound 6-18) (200 mg, 1.06 mmol) were dissolved in methanol 3 mL. Palladium carbon (30 mg) was added thereto, followed by stirring under hydrogen balloon for 12 hours. After the completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure to obtain 2,4-dimethyl-6-(tetrahydrofuran-2-yl)phenol (200 mg, 98%).

Workup

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

Sources & evidence

ORD record
ord-4b7de1dd2efe48be9ceb5ed85cbbaa72
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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