Sulfuric Acid → 4-[4-(2,5-Dichlorobenzoyl)phenoxy]benzene sulfonic acid sodium salt

HRID 2246026Notes

Reaction equation

HRID 2246026 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5].C([O:27][S:28](=O)(=[O:30])[OH:29])(=O)C.S(=O)(=O)(O)O.C(OC(=O)C)(=O)C.[OH-].[Na+:45]>ClCCCl.O.C(O)CC>[Na+:45].[Cl:1][C:2]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:28]([O-:30])(=[O:29])=[O:27])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 3015046Acetyl sulfateHCID 120810592,5-Dichloro-4'-phenoxybenzophenone

Product 1

HCID 237098054-[4-(2,5-Dichlorobenzoyl)phenoxy]benzene sulfonic acid sodium salt

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent3×HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

2,5-dichloro-4′-phenoxybenzophenone (A, 137.3 g, 400 mmol) was put in a 3 L three-necked flask equipped with a stirring device and cooling tube, and 500 mL of 1,2-dichloroethane (1,2-DCE) was added and dissolved. Furthermore, 2 M of acetyl sulfuric acid solution prepared by mixing 56 mL of concentrated sulfuric acid, 152 mL of acetic anhydride, and 400 mL of 1,2-DCE, was added to the flask while stirring, and the reaction was performed in an oil bath at 60° C. After the predetermined period, 300 mL of 1-propanol was added to stop the reaction. Next, the reaction liquid was concentrated to a volume of 400 mL, and NaOH aqueous solution (120 g (3 mol)/water 400 mL) was added. The remaining 1,2-DCE in the reaction liquid was removed by azeotropic distillation, and a transparent light yellow solution was obtained. The light yellow solution was cooled, and deposition was filtered. The deposition was dried in a vacuum at 70° C. to obtain a white fine powder of 4-[4-(2,5-dichlorobenzoyl)phenoxy]benzene sulfonic acid sodium salt (A—SO3Na) shown in Chemical Formula 3. The crude crystal was used in the next process without being purified.

Workup

  1. customequipped with a stirring device
  2. temperaturecooling tube
  3. dissolutiondissolved
  4. additionwas added to the flask
  5. customthe reaction was performed in an oil bath at 60° C
  6. customthe reaction
  7. customNext, the reaction liquid
  8. additionwas added
  9. customwas removed by azeotropic distillation
  10. customa transparent light yellow solution was obtained
  11. temperatureThe light yellow solution was cooled
  12. filtrationdeposition was filtered
  13. customThe deposition was dried in a vacuum at 70° C.

Sources & evidence

ORD record
ord-9ac2f4113fc94bef9359dad66fd4a899
Source dataset
uspto-grants-2010_03
Patent number
US07687187B2

Reaction notes

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