4,6-Di-tert-butyl-5-hydroxybenzofuran → 5-Benzofuranol, 4,6-bis(1,1-dimethylethyl)-2,3-dihydro-

HRID 1900522Notes

Reaction equation

HRID 1900522 reaction equation
[C:1]([C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([C:5]1[C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuran

Product 1

HCID 108686585-Benzofuranol, 4,6-bis(1,1-dimethylethyl)-2,3-dihydro-Yield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4,6-Di-tert-butyl-5-hydroxybenzofuran (6.0 g) was dissolved in acetic acid (50 ml). After addition of 10% Pd on carbon (5.0 g), the solution was stirred under a hydrogen atmosphere (4 atm.) for 15 min. After filtering off the Pd on carbon, the filtrate was concentrated under vacuum. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran [4.4 g (yield, 73%)] as a colorless, fine-grained crystal.

Workup

  1. filtrationAfter filtering off the Pd on carbon
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-a5732fb50af64622b2c6b05b4e9ebaf9
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

Loading…