HCID 14296006, compound → HCID 14143240, compound

HRID 2119715Notes

Reaction equation

HRID 2119715 reaction equation
[C:1]([C:5]1[C:13]([OH:14])=[CH:12][C:8]2[CH:9]=[CH:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([C:5]1[C:13]([OH:14])=[CH:12][C:8]2[CH2:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 14296006HCID 14296006, compound

Product 1

HCID 14143240HCID 14143240, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.07 g of 6-t-butyl-5-hydroxybenzofuran was dissolved in 5 ml of acetic acid and a catalytic amount of 10% palladium on carbon was added. The mixture was stirred under a hydrogen pressure (3.5 kg/cm2) for 6 hours. After the palladium on carbon was filtered off, the solution was concentrated and the concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate) to give 0.05 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran as a white solid (yield 71%).

Workup

  1. filtrationAfter the palladium on carbon was filtered off
  2. concentrationthe solution was concentrated
  3. customthe concentrate was purified by silica gel column chromatography (in n-hexane containing 9% ethyl acetate)

Sources & evidence

ORD record
ord-c40e036a961f4eb1a8fa5cfed9a9623e
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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