5-Benzyloxy-4-t-butyl-2-formylbenzofuran → 4-t-Butyl-5-hydroxy-2-methylbenzofuran

HRID 1452370Notes

Reaction equation

HRID 1452370 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=O)=[CH:14][C:13]=2[C:19]=1[C:20]([CH3:23])([CH3:22])[CH3:21])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:20]([C:19]1[C:13]2[CH:14]=[C:15]([CH3:17])[O:16][C:12]=2[CH:11]=[CH:10][C:9]=1[OH:8])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 234428795-Benzyloxy-4-t-butyl-2-formylbenzofuran

Product 1

HCID 234428664-t-Butyl-5-hydroxy-2-methylbenzofuranYield 68.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5-Benzyloxy-4-tert-butyl-2-formylbenzofuran (700 mg, 2.3 mmol) was dissolved in acetic acid (30 ml) and, after addition of 10% Pd on carbon (700 mg), the solution was stirred under a hydrogen atmosphere (5 arm.) for 8 h. After filtering off the Pd on carbon, the filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was subjected to silica gel chromatography and eluted with a solvent system consisting of a 4:1 mixture of hexane and ethyl acetate to afford 4-tert-butyl-5-hydroxy-2-methylbenzofuran [320 mg (yield, 68%)] as a pale yellow, fine-grained crystal.

Workup

  1. filtrationAfter filtering off the Pd on carbon
  2. washthe filtrate was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with a solvent system
  6. additionconsisting of a 4:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ef353929260a4afb916b371db283a917
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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