Phenol → 4-Tert-butyl-2,3-dihydro-5-benzofuranol

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Reaction Steps

To a solution of 4-tert butyl-5-benzofuranol (0,660 g, 3.47 mmol) 41a in acetic acid (20 mL) is added 10% palladium on carbon (0.130 ) and the mixture hydrogenated overnight at 40 psi. The reaction mixture is taken up in ether (25 mL) and filtered through a bed of Celite to remove the catalyst. The filtrate and washing are diluted with water (100 mL) and ether (50 mL) and the layers separated. The aqueous layer is washed with an additional portion of ether (50 mL) and the combined extracts washed sequentially with 5% NaHCO3 (3×50 mL), water (50 mL), and 20% NaCl (50 mL) then dried (MgSO4) and concentrated. Purification by flash chromatography using 5% ethyl acetate in hexane as eluant gives 4-tert-butyl-2,3-dihydro-5-benzofuranol.

Provenance & Evidence