Methyl iodide → Benzenepropanoic acid, 4-hydroxy-, methyl ester

To a 1000 mL RB flask fitted with magnetic stirrer was charged 250 mL of DMF, 3-(4-Hydroxy-phenyl)-propanoic acid (25.0 g, 150.43 mmol) and K2CO3 (41.58 g, 300.87 mmol). The resulting mixture was stirred at RT for 30 minutes. Methyl Iodide (25.627 g, 180.51 mmol) was added to the resulting mixture which was precooled to 0° C. The resulting mixture was stirred at RT for 3 h. After completion of the reaction (reaction monitored by TLC), the solvent was removed under reduced pressure and the crude mass was dissolved in ethyl acetate (250 mL). The organic layer was washed with water (250 mL), saturated sodium bicarbonate solution (250 mL×2), and saturated brine solution (250 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as yellow color oil (26 g, Yield: 95.9%): MS (ESI, 120 eV): m/z=178.9 (M−H)+; 1H NMR (300 MHz, CDCl3): δ 6.97-7.00 (d, 2H), 6.66-6.69 (d, 2H), 4.94 (s, 1H), 3.59 (s, 3H), 2.78-2.83 (t, 2H), 2.50-2.55 (t, 2H).

1. customTo a 1000 mL RB flask fitted with magnetic stirrer
2. customwas precooled to 0° C
3. stirringThe resulting mixture was stirred at RT for 3 h
4. customAfter completion of the reaction (reaction monitored by TLC)
5. customthe solvent was removed under reduced pressure
6. dissolutionthe crude mass was dissolved in ethyl acetate (250 mL)
7. washThe organic layer was washed with water (250 mL), saturated sodium bicarbonate solution (250 mL×2), and saturated brine solution (250 mL)
8. dry with materialThe organic layer was dried over anhydrous Na2SO4
9. customthe solvent was removed under reduced pressure

ORD record

ord-d53f5ef83efe4210a0f5b07a85f579bf

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2