Sodium Hydroxide → HCID 23083190, compound

HRID 2422294Notes

Reaction equation

HRID 2422294 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:12][CH:11]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23083008HCID 23083008, compound

Product 1

HCID 23083190HCID 23083190, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (5.0 mL) of methyl 3-(4-((3-(2,6-dimethylphenoxy)benzyl)oxy)phenyl)propanoate (0.24 g, 0.62 mmol) in methanol was added 1N aqueous sodium hydroxide solution (1.2 mL), and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2-1/4) to give the title compound (0.15 g, yield 64%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1N hydrochloric acid and water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2-1/4)

Sources & evidence

ORD record
ord-c3f89e9b805a4f6796a41c7988548aa8
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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