Methanol → 5-(2,4-Dimethoxyphenyl)-2,4-pentadienoic acid

HRID 414484Notes

Reaction equation

HRID 414484 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]([O:17]CC)=[O:16].CO.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54051005Ethyl 5-(2,4-dimethoxyphenyl)-2,4-pentadienoate

Product 1

HCID 539851515-(2,4-Dimethoxyphenyl)-2,4-pentadienoic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 9.44 g (36.0 mmol) of said ethyl 5-(2,4-dimethoxyphenyl)-2,4-pentadienoate was added 80 ml of methanol to give a solution. To thesolution was then added a solution of 14.40 g (360 mmol) of sodium hydroxide dissolved in 20 ml of water, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure followed by addition of water and a hydrochloric acid solution to adjust the pH to 1 and extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave 7.70 g (32.9 mmol) of 5-(2,4-dimethoxyphenyl)-2,4-pentadienoic acid.

Workup

  1. customto give a solution
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionfollowed by addition of water
  4. extractionto 1 and extraction with chloroform
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-88180fe91bac4a148f4ee402c5177daf
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Reaction notes

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