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

HRID 2119690Notes

Reaction equation

HRID 2119690 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>C(O)(=O)C.[Pd]>[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 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Under hydrogen atmosphere, a solution of 1.1 g of 5-benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran in 50 ml of acetic acid was stirred with 1.1 g of 10% palladium on carbon for 36 hours. After the palladium on carbon was filtered out, the filtrate was concentrated and the concentrate was purified by silica gel column chromatography (in chloroform) to give 0.6 g of 4-t-butyl-5-hydroxy-2-n-octylbenzofuran as a pale yellow oil (yield 69%).

Workup

  1. filtrationAfter the palladium on carbon was filtered out
  2. concentrationthe filtrate was concentrated
  3. customthe concentrate was purified by silica gel column chromatography (in chloroform)

Sources & evidence

ORD record
ord-240a5819476d4ed7b3828376915ae131
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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