Sodium Hydroxide → HCID 22400483, compound

HRID 260828Notes

Reaction equation

HRID 260828 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:16][CH2:17]/[CH:18]=[CH:19]/[C:20]([O:22]CC)=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>C(O)C.O1CCOCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:16][CH2:17]/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22400506HCID 22400506, compound

Product 1

HCID 22400483HCID 22400483, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (E)-ethyl 4-[1-(4-isobutylphenyl)pentyloxy]-2-butenoate in ethanol and 1,4-dioxane was added a 4N aqueous solution of sodium hydroxide. After being stirred at 80° C. for 5 hours, the mixture was cooled, concentrated and acidified with diluted hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent and silica gel column chromatography of the residue afforded the object compound.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent and silica gel column chromatography of the residue
  7. customafforded the object compound

Sources & evidence

ORD record
ord-65a21e721d9d4555bcd68371b2ab5575
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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