Hexane → Methyl 4-ethenylbenzoate

Participants

Reaction Steps

To a slurry of methyltriphenylphosphonium bromide (10.88 g, 30.46 mmol, 1 eq.) and potassium tert-butoxide (31 mL, 1 M solution in THF, 30.46 mmol, 1 eq.) in THF is added methyl-4-formylbenzoate (5.0 g, 30.46 mmol, 1 eq.). The bright yellow reaction mixture is stirred at room temperature for 5 hrs. Hexane is added and after stirring for 10 minutes, the mixture is filtered and washed twice with hexanes. Solvent is removed in vacuum and the crude oily residue is purified by silica gel chromatography (0-14% ethyl acetate/hexanes) to give 3.76 g of a white oily solid, methyl 4-vinylbenzoate (23.21 mmol, 76.2% yield). 1H NMR (300 MHz, CDCl3): δ 7.99 (2H, d, J=9 Hz), 7.45 (2H, d, J=9 Hz), 6.76 (1H, dd, J=17, 11 Hz), 5.86 (1H, d, J=17 Hz), 5.37 (1H, d, J=11 Hz), 3.91 (3H, s).

Provenance & Evidence