Methyl iodide → Methyl 4-ethenylbenzoate

To a solution of 4-vinylbenzoic acid (Aldrich, 2.18 g, 14.7 mmol) in anhydrous acetonitrile (14.0 mL) was added 1.8-diazabicyclo [5.4.0]undec-7-ene (Aldrich, 2.46 g, 16.2 mmol) and iodomethane (Aldrich, 3.13 g, 2.1 mmol) at 0° C. The reaction mixture was then warmed to room temperature and allowed to stir for 3 h. Ethyl acetate (100 mL) was added to the mixture and the solution was washed with brine (50 mL). The organic phase was then separated and concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane) to give 1.05 g (Y: 44%) of the title product; 1H-NMR (CDCl3): δ8.00 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 6.76 (m, 1H), 5.87 (d, J=17.6 Hz, 1H), 5.38 (d, J=11.0 Hz, 1H), 3.91 (s, 3H); MS (DCI) m/e: 163 (MH+).

1. washthe solution was washed with brine (50 mL)
2. customThe organic phase was then separated
3. concentrationconcentrated in vacuo
4. customThe residue was chromatographed on silica gel (eluted with 5% ethyl acetate in hexane)

ORD-Eintrag

ord-0b775bc4eb8d41efbf5bcc45d9cdf8fd

Quelldatensatz

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05618839