4-(Benzyloxy)-1-(methanesulfonyl)-2-methoxybenzene → 4-(Methanesulfonyl)-3-methoxyphenol

HRID 748893Notes

Reaction equation

HRID 748893 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:11]([O:19][CH3:20])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[O:19][CH3:20])(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 685151294-(Benzyloxy)-1-(methanesulfonyl)-2-methoxybenzene

Product 1

HCID 587855674-(Methanesulfonyl)-3-methoxyphenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 4-benzyloxy-1-methanesulfonyl-2-methoxy-benzene (5.57 g, 19.09 mmol) in MeOH (200 mL), under N2, and add 5% Pd—C (900 mg). Evacuate the reaction vessel and flush with hydrogen gas (3 times). Stir the reaction mixture at room temperature for 3 hours, under 1 atmosphere of hydrogen gas. Filter, concentrate, and purify the reaction mixture by flash column chromatography (silica gel, 30-60% of EtOAc/hexane) to give 3.24 g of 4-methanesulfonyl-3-methoxy-phenol (100%).

Workup

  1. customEvacuate the reaction vessel
  2. customflush with hydrogen gas (3 times)
  3. filtrationFilter
  4. concentrationconcentrate
  5. custompurify the reaction mixture by flash column chromatography (silica gel, 30-60% of EtOAc/hexane)

Sources & evidence

ORD record
ord-614f8a9ad8ca47ec966331f2cb2d83c9
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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