Sulfuric Acid → 2,3,4,5-Tetrafluorobenzoic acid

HRID 622252Notes

Reaction equation

HRID 622252 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:4](C(O)=O)[C:3]=1[C:14]([OH:16])=[O:15].S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[OH-].[Ca+2].[OH-]>O>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 695443,4,5,6-Tetrafluorophthalic acid2×HCID 6093208Calcium HydroxideHCID 6097028Ammonium Sulfate

Product 1

HCID 2975492,3,4,5-Tetrafluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Decarboxylation of 3,4,5,6-tetrafluorophthalic acid was carried out by following the procedure of Example 1, except that 238 g (1.00 mole) of 3,4,5,6-tetrafluorophthalic acid, 13.8 g (0.140 mole) of sulfuric acid, 5.5 g (0.042 mole) of ammonium sulfate, 22.2 g (0.30 mole) of calcium hydroxide, and 480 g of water were used [pH 1.89 at 70° C. at the time of charging]. This example was found to have produced 2,3,4,5-tetrafluorobenzoic acid in a yield of 95.4 mole %.

Workup

  1. customat 70° C.

Sources & evidence

ORD record
ord-703410e45d934f32a802899b7c803892
Source dataset
uspto-grants-1988_09
Patent number
US04769492

Reaction notes

Loading…