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

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).

1. customcompletion of reaction
2. filtrationThe resultant was filtered
3. concentrationsubjected to vacuum concentration
4. concentrationAfter the concentration, 50 mL of a 1 N sodium hydroxide aqueous solution
5. additionwas added
6. stirringthe resultant was stirred for one hour
7. customAfter reaction
8. customa reaction solution thus obtained
9. filtrationwas filtered
10. additionwas added
11. customA precipitate thus produced
12. filtrationwas collected by filtration
13. washwashed with a small amount of chloroform

ORD record

ord-592d64f93fe24d7e9cd6d5630f0c0c7c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697332B2