Sodium Hydroxide → HCID 57626302, compound

Participants

Reaction Steps

To a magnetically stirred solution of ethyl 2-fluorobenzaldehyde (11.7 ml, 110 mmol) and ethylglyoxalate (11.1 ml, 100 mmol) in ethanol (50 ml) was slowly added a solution of sodium hydroxide (4.4 g (110 mmol) in 50 ml water) in a nitrogen atmosphere while the temperature was kept between 0° C. and 10° C. After stirring for another 45 minutes the reaction mixture was allowed to attain room temperature and stirred for 2 hours. The formed precipitate was collected by filtration and successively washed with ethanol and a 1N HCl solution (200 ml) and subsequently dried to give E-2-oxo-4-(2-fluorophenyl)-but-3-enoic acid (11.1 gram, 57% yield) Melting point: 100-102.5° C. 1H-NMR (400 MHz, CDCl3) δ 7.13-7.27 (m, 2H), 7.45-7.53 (m, 1H) 7.66-7.74 (m, 2H), 8.26 (d, J=16, 1H), invisible —OH proton.

Provenance & Evidence