Potassium Hydroxide → 2-Furancarboxylic acid, 5-methyl-

Methyl 5-methyl-2-furoate (3.68 g, 26.29 mmol) in methanol (30 ml) was treated with a solution of potassium hydroxide (2.80 g, 50.0 mmol) in water (15 ml) and the mixture stirred for 2 h at room temperature. The methanol was evaporated in vacuo, the residue dissolved in water and washed with ethyl acetate. The aqueous phase was acidified with SN hydrochloric acid, and the product extracted with ethyl acetate (x3). The combined organic solutions were dried and concentrated to yield the title compound as a yellow solid (3.12 g, 94%); m.p. 110-112° C.; (Found: M+, 126.0312. C6H6O3 requires M+ 126.0317); νmax (CH2C12) 3300-2700, 1688, 1524, 1424, 1305, 1210 and 1167 cm-1 ; δH (CDCl3, 90 MHz) 2.40 (3 H, s), 6.15 (1 H, d, J 4 Hz) and 7.22 (1 H, d, J 4 Hz).

1. customThe methanol was evaporated in vacuo
2. dissolutionthe residue dissolved in water
3. washwashed with ethyl acetate
4. extractionthe product extracted with ethyl acetate (x3)
5. customThe combined organic solutions were dried
6. concentrationconcentrated

ORD record

ord-876d93a4846146a4966eb33d7b266495

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001997