Sodium Hydroxide → HCID 58903113, compound

HRID 273400Notes

Reaction equation

HRID 273400 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=3)[CH:10]=2)=[C:4]([CH3:29])[CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:22]=3)[CH:10]=2)=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57413460HCID 57413460, compound

Product 1

HCID 58903113HCID 58903113, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl]propanoate (0.18 g, 0.46 mmol) in methanol (2 mL) and tetrahydrofuran (4 mL) was added 1 N aqueous sodium hydroxide solution (0.91 mL) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated and the residue was diluted with ethyl acetate, washed with 1 N hydrochloric acid and saturated brine, dried and concentrated under reduced pressure. The residue was crystallized from hexane/ethyl acetate=4/1 to give the title compound (0.13 g, yield 74%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1 N hydrochloric acid and saturated brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from hexane/ethyl acetate=4/1

Sources & evidence

ORD record
ord-4ab184710e924a2485bf942c303df666
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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