Tetrahydrofuran → 2-Methyl-6-(tetrahydro-3-furanyl)phenol

HRID 63388Notes

Reaction equation

HRID 63388 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=2[OH:13])=[CH:2]1.O1CCCC1>CO.[C].[Pd]>[CH3:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[C:7]=1[OH:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 121871312-(3-Furanyl)-6-methylphenol2×

Product 1

HCID 900026522-Methyl-6-(tetrahydro-3-furanyl)phenolYield 93.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(furan-3-yl)-6-methylphenol (Compound 6-9) (173 mg, 0.70 mmol) and palladium carbon (25 mg, 15%) were dissolved in methanol:tetrahydrofuran=1 mL:1 mL, followed by stirring under hydrogen balloon for 48 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 (hexane:ethyl acetate=3:1) to obtain 2-methyl-6-(tetrahydrofuran-3-yl)phenol (117 mg, 93%).

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 (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-02158d4e5a46465c9e4a29c1f9aca2a6
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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