3-(1-Hexenyl)-4-methoxybenzoic acid → 3-Hexyl-4-methoxybenzoic acid

HRID 850438Notes

Reaction equation

HRID 850438 reaction equation
[CH:1]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10]([OH:12])=[O:11])=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H]>[C].[Pd].C(O)C>[CH2:1]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 538972933-(1-Hexenyl)-4-methoxybenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 193634153-Hexyl-4-methoxybenzoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

3-(1-Hexenyl)-4-methoxybenzoic acid (160 mg, 0.683 mmol) and ethanol (7 ml) were mixed, and to this solution was added 10% palladium-carbon catalyst (30 mg). The mixture was stirred at room temperature for 3 hours in a steam of hydrogen. The palladium-carbon catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by washing with hexane to give 3-hexyl-4-methoxybenzoic acid (116 mg, 72%) as colorless crystals.

Workup

  1. filtrationThe palladium-carbon catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified
  4. washby washing with hexane

Sources & evidence

ORD record
ord-7dadbe6512b44e339eb1675cb8f5aaa6
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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