Acetic Acid → 2-Fluoro-4-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred glacial acetic acid solution of Na2Cr2 07 (80.46 g, 0.26 mol) in a 2 1 beaker was added 2-fluoro-4-nitrotoluene (31.03 g, 0.2 mol) followed during 10 minutes by concentrated H2SO4 (200 g). The initially bright orange solution became viscous and black and then boiled at just over 100° C. The resulting green slurry was heated for a further 1 hour at 90° C. Water (236 ml) was added and the resulting solution was cooled to 0° C. to give pale green crystals which were recovered by filtration and washed sparingly with cold water. The product (22.14 g) was recrystallised from water (200 ml) as pale green microneedles (21.16 g, 57.2%). M.P. 175°-178° C., Lit. F. C. Schmelkes and M. Rubin, J. Am. Chem. Soc. 66, 1631, (1944), 176°-177° C.

Provenance & Evidence