6-(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid → 6-(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)hexanoic acid

HRID 367307Notes

Reaction equation

HRID 367307 reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[C].[Pd]>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 536842956-(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid

Product 1

HCID 232880446-(4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)hexanoic acidYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.11 g of 6-(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)-5-hexenoic acid synthesized in Example 77 in 10 ml of ethyl acetate was added a catalytic amount of 10% palladium-carbon, and the mixture was stirred for 24 hours under a hydrogen atmosphere. After the catalyst was filtered off, the filtrate was concentrated to give 0.10 g of 6-(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)hexanoic acid as a colorless viscous liquid (yield 90%).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f33000d9f6064a99ab28606740c99414
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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