Methanol → 3-[4-(Benzyloxy)-2-methoxyphenyl]-3-cyanopropanoic acid

Temperature

70 °C

To a 25 mL RB flask fitted with magnetic stirrer was charged with methanol (20 mL) and water (5 mL). To the stirred solvent was added diethyl [4-(benzyloxy)-2-methoxybenzylidene]propanedioate (0.775 g, 2.02 mmol), followed by potassium cyanide (0.262 g, 4.04 mmol). The RM was heated at 70° C. for 2 h. The RM was concentrated, diluted with saturated NaHCO3 solution (50 mL) and washed with ethyl acetate (50 mL×2). The aqueous layer was acidified to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (50 mL×2). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown liquid. (0.62 g, yield: 100.0%).

1. customTo a 25 mL RB flask fitted with magnetic stirrer
2. concentrationThe RM was concentrated
3. additiondiluted with saturated NaHCO3 solution (50 mL)
4. washwashed with ethyl acetate (50 mL×2)
5. extractionextracted with ethyl acetate (50 mL×2)
6. washThe organic layer was washed with water (50 mL) and saturated brine solution (50 mL)
7. dry with materialThe organic layer was dried over anhydrous Na2SO4
8. customthe solvent was removed under reduced pressure
9. customThe product was obtained as brown liquid

ORD record

ord-9dc5433c51c24dbca3a7f2b83180c365

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2