HCID 58903181, compound → HCID 57413290, compound

HRID 273403Notes

Reaction equation

HRID 273403 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2]>CO.O1CCCC1.[OH-].[Na+].C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2]

Participants

6

Reactant 1

HCID 58903181HCID 58903181, compound

Product 1

HCID 57413290HCID 57413290, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-[4-[[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy]phenyl]propanoate (0.12 g, 0.26 mmol) was dissolved in a mixed solution of methanol (2 mL) and tetrahydrofuran (4 mL), and 1 N aqueous sodium hydroxide solution (0.52 mL) was added at room temperature with stirring. The mixture was stirred at the same temperature for 2 hrs. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed successively with 1 N hydrochloric acid, water and saturated brine, dried and concentrated under reduced pressure. The residue was crystallized from hexane/ethyl acetate=4/1 to give the title compound (0.087 g, yield 75%) as colorless crystals.

Workup

  1. additionwas added at room temperature
  2. stirringThe mixture was stirred at the same temperature for 2 hrs
  3. customAfter the completion of the reaction
  4. washwashed successively with 1 N hydrochloric acid, water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane/ethyl acetate=4/1

Sources & evidence

ORD record
ord-60f115ff9d87415dba621f1e44b82a8b
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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