2-[5-(2,4-Diisobutoxybenzoyl)-2-isobutoxyphenyl]acetic acid → 2-[5-(2,4-Diisobutoxybenzyl)-2-isobutoxyphenyl]acetic acid

HRID 2249618Notes

Reaction equation

HRID 2249618 reaction equation
[CH2:1]([O:5][C:6]1[CH:28]=[C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH:26]=[CH:25][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[CH:15]=1)=O)[CH:2]([CH3:4])[CH3:3].[H][H]>C(O)C.[C].[Pd]>[CH2:1]([O:5][C:6]1[CH:28]=[C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH:26]=[CH:25][C:7]=1[CH2:8][C:10]1[CH:11]=[CH:12][C:13]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[CH:15]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 178165642-[5-(2,4-Diisobutoxybenzoyl)-2-isobutoxyphenyl]acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 178164592-[5-(2,4-Diisobutoxybenzyl)-2-isobutoxyphenyl]acetic acidYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 2 ml of ethanol is dissolved 200 mg of 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]acetic acid. After adding 40 mg of 5% palladium-carbon, the mixture thus obtained is stirred at ambient temperature for one hour in a stream of hydrogen gas. The reaction mixture is filtered with Celite, and the solvent is distilled off under reduced pressure from the filtrate. The residue thus obtained is purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=4:1] to obtain 140 mg of 2-[5-(2,4-diisobutoxybenzyl)-2-isobutoxyphenyl]acetic acid as a colorless oily product.

Workup

  1. customthe mixture thus obtained
  2. filtrationThe reaction mixture is filtered with Celite
  3. distillationthe solvent is distilled off under reduced pressure from the filtrate
  4. customThe residue thus obtained
  5. customis purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-e810e911102646f3a6e08da4d5ce5858
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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