3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid → Methyl Ferulate

Temperature

-25 °C

100 g of 4-hydroxy-3-methoxycinnamic acid were dissolved in 1 l of methanol and treated with 14.4 ml of concentrated sulphuric acid. The solution was heated under reflux for 2.5 hrs. Subsequently, the majority of the methanol (about 750 ml) was distilled off and the residue remaining was poured into 1 l of water. Then, the mixture was extracted three times with 500 ml of ethyl acetate each time and the organic phases were combined, washed twice with 250 ml of 10% sodium bicarbonate solution each time, dried over sodium sulphate, filtered and evaporated. The residue was dissolved in 800 ml of methanol, filtered and, for crystallization, cooled to -25° C. The crystals were thereupon filtered off under suction, washed with 100 ml of cold methanol and dried in a high vacuum at room temperature. This gave 54.7 g of yellowish colored crystals.

1. temperatureThe solution was heated
2. temperatureunder reflux for 2.5 hrs
3. distillationSubsequently, the majority of the methanol (about 750 ml) was distilled off
4. additionthe residue remaining was poured into 1 l of water
5. extractionThen, the mixture was extracted three times with 500 ml of ethyl acetate each time
6. washwashed twice with 250 ml of 10% sodium bicarbonate solution each time
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. customevaporated
10. dissolutionThe residue was dissolved in 800 ml of methanol
11. filtrationfiltered and, for crystallization
12. filtrationThe crystals were thereupon filtered off under suction
13. washwashed with 100 ml of cold methanol
14. customdried in a high vacuum at room temperature

ORD record

ord-2592e918f20b4099a857b5357e67f944

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05965761