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

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Reaction Steps

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.

Provenance & Evidence