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

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.

1. customthe mixture hydrogenated overnight
2. filtrationfiltered through a bed of Celite
3. customto remove the catalyst
4. washThe filtrate and washing
5. additionare diluted with water (100 mL) and ether (50 mL)
6. customthe layers separated
7. washThe aqueous layer is washed with an additional portion of ether (50 mL)
8. washthe combined extracts washed sequentially with 5% NaHCO3 (3×50 mL), water (50 mL), and 20% NaCl (50 mL)
9. dry with materialthen dried (MgSO4)
10. concentrationconcentrated
11. customPurification by flash chromatography

ORD record

ord-b7187d3c7b84448b8a7c63dbdc06ad5f

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04966907