Acetic Acid → 2-Fluoro-4-nitrobenzoic acid

HRID 2254571Notes

Reaction equation

HRID 2254571 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[F:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8]C=1C.OS(O)(=O)=O>O>[F:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:2]=1[C:1]([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 740252-Fluoro-4-nitrotoluene

Product 1

HCID 3026792-Fluoro-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  1. customjust over 100° C
  2. temperaturethe resulting solution was cooled to 0° C.
  3. customto give pale green crystals which
  4. filtrationwere recovered by filtration
  5. washwashed sparingly with cold water
  6. customThe product (22.14 g) was recrystallised from water (200 ml) as pale green microneedles (21.16 g, 57.2%)
  7. custom66, 1631, (1944), 176°-177° C.

Sources & evidence

ORD record
ord-f5420df4161246bfbbabd83875427010
Source dataset
uspto-grants-1993_08
Patent number
US05236927

Reaction notes

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