Potassium Carbonate → 3-(2-Hydroxy-4-methoxyphenyl)prop-2-enoic acid

Participants

Reaction Steps

In a 100 mL flask, 2.00 g of potassium carbonate was added to 15 mL of methanol. In a 50 mL flask, 2.67 g (6.2 mmol) of ethoxycarbonylmethyl(triphenyl)phosphonium bromide and 945 mg (6.2 mmol) of 2-hydroxy-4-methoxybenzaldehyde were dissolved in 10 mL of methanol. The resultant was gradually added to a well-stirred potassium carbonate solution in a dropwise manner. After stirring the resultant for 3 hours, completion of reaction was confirmed by TLC. The resultant was filtered to exclude potassium carbonate and subjected to vacuum concentration. After the concentration, 50 mL of a 1 N sodium hydroxide aqueous solution was added thereto and the resultant was stirred for one hour. After reaction was completed, a reaction solution thus obtained was filtered to exclude triphenylphosphine oxide, and concentrated hydrochloric acid was added thereto in a dropwise manner to make the reaction solution an acidic solution. A precipitate thus produced was collected by filtration and washed with a small amount of chloroform, thereby obtaining 1.00 g of 2-hydroxy-4-methoxycinnamic acid. Then, in a 100 mL three-necked flask, 1.00 g (6.0 mmol) of 2-hydroxy-4-methoxycinnamic acid was dissolved in 40 mL of dehydrated tetrahydroxyfuran, and 1.41 g (7.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) was added thereto. After 30 minutes, 0.72 ml (7.2 mmol) of piperidine was added thereto. After reaction was completed, a reaction solution thus obtained was condensed and dissolved in water. The resulting solution was extracted with chloroform to obtain an extract. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution, 1 N hydrochloric acid and then saturated saline, and then washed with a small amount of chloroform, thereby obtaining 1.03 g of a compound represented by the following formula (14).

Provenance & Evidence