Methanesulfonic Acid → Methyl 3-cyano-3-(4-hydroxyphenyl)propanoate

To a 50 mL RB flask fitted with magnetic stirrer was charged with methanol (15 mL). To the stirred solvent was added 3-cyano-3-(4-hydroxyphenyl)propanoic acid (0.6 g, 3.1 mmol), followed by the addition of methanesulfonic acid (1 mL). The reaction mixture was refluxed for 1 h. After completion of the reaction, the reaction mixture was concentrated to distill off the solvent. Water (10 mL) was added and extracted with ethyl acetate (25 mL). The organic layer was washed with water (5 mL) and saturated brine solution (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow liquid (0.6 g, yield: 93.3%). 1H NMR (300 MHz, CDCl3): δ 7.13-7.15 (d, 2H), 6.75-6.78 (d, 2H), 4.14-4.19 (t, 1H), 3.65 (s, 3H), 2.89-2.97 (m, 1H), 2.71-2.79 (m, 1H).

1. customTo a 50 mL RB flask fitted with magnetic stirrer
2. temperatureThe reaction mixture was refluxed for 1 h
3. customAfter completion of the reaction
4. concentrationthe reaction mixture was concentrated
5. distillationto distill off the solvent
6. additionWater (10 mL) was added
7. extractionextracted with ethyl acetate (25 mL)
8. washThe organic layer was washed with water (5 mL) and saturated brine solution (5 mL)
9. dry with materialThe organic layer was dried over anhydrous Na2SO4
10. customthe solvent was removed under reduced pressure

ORD record

ord-de803f82d4574e32a657db971e3a27b1

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2