Hydrochloric Acid → 2-{5-[(2,4-Diisobutoxyphenyl)(hydroxy)methyl]-2-isobutoxyphenyl}-acetic acid

HRID 2249616Notes

Reaction equation

HRID 2249616 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:9])[CH:2]([CH3:4])[CH3:3].[BH4-].[Na+].[Cl-].[Li+].Cl>CO.O.C(Cl)(Cl)Cl>[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[CH:8]([OH:9])[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydride2×HCID 178165642-[5-(2,4-Diisobutoxybenzoyl)-2-isobutoxyphenyl]acetic acid

Product 1

HCID 576843802-{5-[(2,4-Diisobutoxyphenyl)(hydroxy)methyl]-2-isobutoxyphenyl}-acetic acidYield 49.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

In 2 ml of methanol is dissolved 100 mg of 2-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]acetic acid. After adding 18 mg of sodium borohydride at 5-10° C., the mixture thus obtained is stirred at 50-60° C. for one hour. Then, 40 mg of sodium borohydride and 40 mg of lithium chloride are further added at ambient temperature, and the mixture thus obtained is stirred at 50-60° C. for two hours. Chloroform and water are added to the reaction mixture, pH is adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is successively washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 50 mg of 2-{5-[(2,4-diisobutoxyphenyl)(hydroxy)methyl]-2-isobutoxyphenyl}-acetic acid is obtained as a colorless oily product.

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at 50-60° C. for two hours
  4. customthe organic layer is separated
  5. washThe organic layer is successively washed with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-4925ea3363ae4cd391512edc94ca8433
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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