Methyl iodide → Methyl 3-(Allyloxy)-5-methoxybenzoate

Temperature

70 °C

To a solution of 3-allyloxy-5-hydroxy-benzoic acid methyl ester (la) (10.25 g, 49.2 mmol) in DMF (20 mL) was added methyl iodide (3.67 mL, 59.1 mmol) and K2CO3 (13.6 g, 98.5 mmol). The reaction mixture was stirred at 70° C. for 2 hr, cooled to room temperature. The mixture was quenched with H2O (150 mL) and extracted with EtOAc (2×150 mL). The organic layers were washed with H2O (2×150 mL), dried over MgSO4 and concentrated to give a pale yellow oil which was purified by flash column chromatography eluting with 10% EtOAc in hexane to give a colorless oil (9.63 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ 7.11-7.24 (m, 2 H) 6.68 (t, J=2.40 Hz, 1 H) 5.91-6.17 (m, 1 H) 5.38-5.51 (m, 1 H) 5.31 (dd, J=10.48, 1.39 Hz, 1 H) 4.52-4.61 (m, 2 H) 3.91 (s, 3 H) 3.83 (s, 3 H); LCMS for C12H14O4 m/z 223.0 (M+H)+.

1. temperaturecooled to room temperature
2. customThe mixture was quenched with H2O (150 mL)
3. extractionextracted with EtOAc (2×150 mL)
4. washThe organic layers were washed with H2O (2×150 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customto give a pale yellow oil which
8. customwas purified by flash column chromatography
9. washeluting with 10% EtOAc in hexane

ORD record

ord-5ea47bcfeee442d4ad96e439cf60eda6

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119624B2