Hydrochloric Acid → HCID 68986077, compound

HRID 2249650Notes

Reaction equation

HRID 2249650 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[C:17]([C:24]1[CH:25]=[CH:26][C:27]([O:35][CH2:36][CH:37]([CH3:39])[CH3:38])=[C:28]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:29]=1)=[CH:18][C:19]([O:21]CC)=[O:20])[CH:2]([CH3:4])[CH3:3].[H][H].[OH-].[Na+].Cl>C(O)C.[C].[Pd].O.C(Cl)(Cl)Cl>[C:32]([CH2:31][CH2:30][C:28]1[CH:29]=[C:24]([CH:17]([C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:11][C:6]=2[O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:18][C:19]([OH:21])=[O:20])[CH:25]=[CH:26][C:27]=1[O:35][CH2:36][CH:37]([CH3:38])[CH3:39])([OH:34])=[O:33]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68984654HCID 68984654, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68986077HCID 68986077, compoundYield 92.8%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In 6 ml of ethanol is dissolved 0.60 g of 3-{5-[1-(2,4-diisobutoxyphenyl)-3-ethoxy-3-oxo-1-propenyl]-2-isobutoxyphenyl}propanoic acid. After adding 0.12 g of 5% palladium-carbon, the mixture is stirred at ambient temperature for one hour in a stream of hydrogen. The reaction mixture is filtered with Celite, and the solvent is distilled off from the filtrate under a reduced pressure to obtain a crude product. The crude product is dissolved in 4 ml of ethanol, 0.7 ml of 5 mol/L sodium hydroxide is added, and the mixture thus obtained is stirred at ambient temperature for one hour. Chloroform and water are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 0.53 g of 3-[3-(2-carboxyethyl)-4-isobutoxyphenyl]-3-(2,4-diisobutoxyphenyl)propanoic acid is obtained as a white foaming product.

Workup

  1. filtrationThe reaction mixture is filtered with Celite
  2. distillationthe solvent is distilled off from the filtrate under a reduced pressure
  3. customto obtain a crude product
  4. customthe mixture thus obtained
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e294eb20529442db5775745ff34c66f
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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