Potassium Hydroxide → (E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid

HRID 1527683Notes

Reaction equation

HRID 1527683 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1/[CH:15]=[C:16](\[CH3:22])/[C:17]([O:19]CC)=[O:18].[OH-].[K+]>CCO>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1/[CH:15]=[C:16](\[CH3:22])/[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 46180044HCID 46180044, compound

Product 1

HCID 46180242(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acidYield 83.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Emmons ester 28a (0.231 g, 0.769 mmol) was dissolved in EtOH (10.0 mL) and then KOH (0.400 g, 7.13 mmol) was added to the reaction. The reaction was heated to boiling and stirred at this temperature for 30 minutes. The reaction was then cooled, acidified, and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, and condensed. The resulting acid was then used as crude, or can be purified via flash chromatography (1:3 EtOAc:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes to provide 29a (0.175 g, 0.643 mmol, 83%) as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureThe reaction was then cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customcondensed
  8. customcan be purified via flash chromatography (1:3 EtOAc:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes

Sources & evidence

ORD record
ord-007ced3b95dc4ae28d04bbdd4f395446
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

Loading…