Hydrochloric Acid → HCID 68989050, compound

HRID 2249649Notes

Reaction equation

HRID 2249649 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].[OH-].[Na+].C(Cl)(Cl)Cl.Cl>C(O)C.O1CCCC1.O>[C:32]([CH2:31][CH2:30][C:28]1[CH:29]=[C:24]([C: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])=[CH: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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 68984654HCID 68984654, compound

Product 1

HCID 68989050HCID 68989050, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 7 ml of ethanol and 3 ml of tetrahydrofuran is dissolved 0.79 g of 3-{5-[1-(2,4-diisobutoxyphenyl)-3-ethoxy-3-oxo-1-propenyl]-2-isobutoxyphenyl}propanoic acid. After adding 8 ml of 5 mol/L sodium hydroxide solution, the mixture thus obtained is stirred at ambient temperature for 2.5 hours and then at 60° C. for 1.5 hours. 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 thus obtained 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. The residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1) to obtain 0.58 g of 3-[3-(2-carboxyethyl)-4-isobutoxyphenyl]-3-(2,4-diisobutoxyphenyl)-2-propenoic acid as a light yellow foaming product.

Workup

  1. customthe mixture thus obtained
  2. waitat 60° C. for 1.5 hours
  3. customthe organic layer is separated
  4. customThe organic layer thus obtained
  5. washis washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-615013d4270842f5af6ad679513f7883
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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