4-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid → 4-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-benzoic acid

HRID 129261Notes

Reaction equation

HRID 129261 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[CH2:15])[CH:5]=[CH:4][C:3]1=2.[H][H]>[Pd].C(O)C>[CH3:25][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH3:15])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 99057294-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 103149774-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-benzoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The olefin 48 (0.0105 g, 0.0314 mmol) was hydrogenated over 5% palladium on charcoal (1 mg) in 0.5 mL of ethanol at room temperature and atmospheric pressure. After one equivalent (0.7 mL) of hydrogen was taken up, the catalyst was removed by filtration through a small Celite pad. The solvent was removed in vacuo to give the crude acid as a white solid (0.019 g). Recrystallization from benzene-hexane afforded the desired acid 49 as a white crystalline solid (0.0078 g, 74%): m.p. 186°-188° C. The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Workup

  1. customthe catalyst was removed by filtration through a small Celite pad
  2. customThe solvent was removed in vacuo
  3. customto give the crude acid as a white solid (0.019 g)
  4. customRecrystallization from benzene-hexane

Sources & evidence

ORD record
ord-85c84f096f4446a890883767bd0ef82b
Source dataset
uspto-grants-1995_11
Patent number
US05466861

Reaction notes

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