2-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenol → 2,4-dimethyl-6-(tetrahydro-2H-pyran-4-yl)phenol

HRID 63392Notes

Reaction equation

HRID 63392 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:8]=2[OH:15])[CH2:3][CH2:2]1>CO.[C].[Pd]>[CH3:14][C:9]1[CH:10]=[C:11]([CH3:13])[CH:12]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:8]=1[OH:15]

Participants

4

Reactant 1

HCID 900035562-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenol2×

Product 1

HCID 900027112,4-dimethyl-6-(tetrahydro-2H-pyran-4-yl)phenolYield 66.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(3,6-dihydro-2H-pyran-4-yl)-4,6-dimethylphenol (Compound 6-17) (234 mg, 1.14 mmol) was dissolved in methanol. Palladium carbon (92 mg, 40 wt %) was added thereto, followed by stirring under hydrogen balloon for 24 hours. After the completion of the reaction, the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1) to obtain 2,4-dimethyl-6-(tetrahydro-2H-pyran-4-yl)phenol (156 mg, 66%) as a white solid.

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. customThe residue was purified by column chromatography (silica gel; hexane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-c34751b68bac4073ab56c74b8220c851
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

Loading…