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

HRID 1376968Notes

Reaction equation

HRID 1376968 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%)] as 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-61e6a3a0f08f49d88c65abe0fa062433
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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