Ethanol → HCID 67327375, compound

HRID 1023361Notes

Reaction equation

HRID 1023361 reaction equation
CCO.[CH3:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:14][N:13]=2)[CH:8]=[CH:7][C:6]=1/[CH:27]=[CH:28]/[C:29]([O:31]CCCC)=[O:30].[OH-].[Na+]>O>[CH3:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:14][N:13]=2)[CH:8]=[CH:7][C:6]=1/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 86673392HCID 86673392, compound

Product 1

HCID 67327375HCID 67327375, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an EtOH (50 mL) solution of butyl (E)-3-[2-methyl-4-({5-[(4-methylbenzyl)-oxy]pyridin-2-yl}oxy)phenyl]prop-2-enoate (4.67 g) was added 5 M NaOH (3.25 mL) at room temperature. After stirring for 14 hours, 5 M NaOH (1.08 mL) and water (25 mL) were added, and then the reaction mixture was refluxed for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in water, and neutralized with 6 M HCl at 0° C. The resulting precipitate was collected by filtration and dried to afford (E)-3-[2-methyl-4-({5-[(4-methylbenzyl)oxy]pyridin-2-yl}oxy)phenyl]prop-2-enoic acid as a colorless solid (4.06 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. customneutralized with 6 M HCl at 0° C
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-9852eee00fef4fe58c94f0f9d85226e0
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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