5-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran → 4-Tert-butyl-5-hydroxy-2-octylbenzofuran

HRID 1452352Notes

Reaction equation

HRID 1452352 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][C:13]=2[C:25]=1[C:26]([CH3:29])([CH3:28])[CH3:27])C1C=CC=CC=1>[Pd].C(O)(=O)C>[C:26]([C:25]1[C:13]2[CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:16][C:12]=2[CH:11]=[CH:10][C:9]=1[OH:8])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 543087225-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran

Product 1

HCID 234428644-Tert-butyl-5-hydroxy-2-octylbenzofuranYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% Palladium on carbon (1.1 g) was added to a solution of 5-benzoxy-4-tert-butyl-2-(1-octenyl)benzofuran (1.1 g, 2.9 mmol) in acetic acid (50 ml), and the mixture was stirred for 36 h under a hydrogen atmosphere. After filtering off the Pd on carbon, the solvent was distilled off with an evaporator. The concentrate was purified by silica gel chromatography (chloroform) to afford 4-tert-butyl-5-hydroxy-2-octylbenzofuran [600 mg (yield, 69%)] a pale yellow oil.

Workup

  1. filtrationAfter filtering off the Pd on carbon
  2. distillationthe solvent was distilled off with an evaporator
  3. customThe concentrate was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-56572f42f9884a46a9b00c5e45ac038c
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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