Hydrochloric Acid → HCID 57684387, compound

HRID 2249628Notes

Reaction equation

HRID 2249628 reaction equation
[OH:1][C:2]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[C:10]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[CH:11]=1)=[O:5].[OH-].[Na+].O.Cl>C(O)C.C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:11]=1)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 17816466HCID 17816466, compound

Product 1

HCID 57684387HCID 57684387, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

In 155 ml of ethanol is dissolved 30.9 g of methyl 3-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isobutoxyphenyl]propanoate, to which is added 44 ml of 5 mol/L solution of sodium hydroxide. The mixture is stirred at ambient temperature for one hour. Water, followed by chloroform, is 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, 29.5 g of 3-[5-(2-hydroxy-4-isobutoxybenzoyl)-2-isobutoxyphenyl]-propanoic acid is obtained as a yellow-white colored solid product.

Workup

  1. additionis added to the reaction mixture, pH
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a64526595a54c2fb46bdd6b3a6bc28b
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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