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

HRID 63391Notes

Reaction equation

HRID 63391 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[C:8]([CH3:14])[CH:7]=2)=[CH:2]1.CO>O1CCCC1.[C].[Pd]>[CH3:12][C:10]1[CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[CH:7]=[C:8]([CH3:14])[C:9]=1[OH:13]

Participants

5

Reactant 2

HCID 887MethanolHCID 900025234-(3-Furanyl)-2,6-dimethylphenol2×

Product 1

HCID 900024642,6-Dimethyl-4-(tetrahydro-3-furanyl)phenolYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(furan-3-yl)-2,6-dimethylphenol (Compound 6-5) (110 mg, 0.74 mmol) were dissolved in tetrahydrofuran:methanol=1 mL:1 mL. Palladium carbon (15 mg, 15%) was added thereto, followed by stirring under hydrogen balloon for 18 hours. After the completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure to obtain 2,6-dimethyl-4-(tetrahydrofuran-3-yl)phenol (74 mg, 72%).

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-5f37847a3b9e44d09520746a923ab6c9
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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