3-(5-Methyl-2-furanyl)-2-propenoic acid → 3-(5-Methyl-furan-2-yl)-propionic acid

14.6 g of β-(5-methyl-2-furyl) acrylic acid, prepared in accordance with the procedures of Example 1, were dissolved in 100 ml H2O containing 4 g of NaOH. 10 g of Raney nickel alloy were then added. The resulting suspension was stirred in an ice-bath and a solution of 8 g of NaOH and 30 ml H2O was slowly added to the stirred solution, while the temperature thereof is maintained at below 20° C. On completion of the addition of the NaOH to the reaction mixture the temperature was permitted to rise slowly to 30° C. The reaction mixture was maintained at this temperature for 2 hours. Thereafter the reaction mixture was filtered with the filtrate being acidified with diluted HCl and extracted with ethyl acetate. The resulting extract was washed with water until neutral, dried and evaporated. The residue, on recrystallization from petroleum ether (boiling point--40°-60° C.), yielded 6.7 g (45% yield) of β-(5-methyl-2-furyl) propionic acid. Chromatography on the mother liquor on a column of silica gel and eluting with petroleum ether (boiling point--40°-60° C.) gave a further yield of 2.5 g (17%) of the pure acid melting at 56°-58° C.

1. temperaturethereof is maintained at below 20° C
2. customto rise slowly to 30° C
3. temperatureThe reaction mixture was maintained at this temperature for 2 hours
4. filtrationThereafter the reaction mixture was filtered with the filtrate
5. extractionextracted with ethyl acetate
6. extractionThe resulting extract
7. washwas washed with water until neutral,
8. customdried
9. customevaporated
10. customThe residue, on recrystallization from petroleum ether (boiling point--40°-60° C.)

ORD record

ord-d13c185094b84b8ea294f78d61760d02

Source dataset

uspto-grants-1985_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04507290