Sulfuric Acid → HCID 57667966, compound

HRID 2191632Notes

Reaction equation

HRID 2191632 reaction equation
S(=O)(=O)(O)O.N[C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].N([O-])=O.[Na+].[I-:27].[K+]>C(OCC)(=O)C.O.C(O)(=O)C>[I:27][C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 57667856HCID 57667856, compound

Product 1

HCID 57667966HCID 57667966, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of water 6.0 mL, acetic acid 10 mL and concentrated sulfuric acid 0.95 mL of 2-amino-4-phenoxybenzoic acid 2.0 g was added water 2.0 mL solution of sodium nitrite 0.66 g at 4° C., and it was stirred at same temperature for 30 minutes. The reaction mixture was added dropwise to water 30 mL solution of potassium iodide 3.2 g at same temperature, and it was stirred at room temperature for 3 hours. Ethyl acetate was added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate:acetic acid=80:20:1] to give 2-iodo-4-phenoxybenzoic acid 1.6 g of red solid.

Workup

  1. stirringwas stirred at room temperature for 3 hours
  2. customThe organic layer was separated
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0a522d928e934847a79075bf56cd10a2
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

Loading…