Hydrochloric Acid → HCID 19387648, compound

HRID 248113

Reaction equation

HRID 248113 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+].Cl[C:16]1[CH:30]=[CH:29][C:19]([C:20]([C:22]2[CH:27]=[CH:26][C:25](Cl)=[CH:24][CH:23]=2)=[O:21])=[CH:18][CH:17]=1.Cl>CN(C=O)C.O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][C:16]2[CH:30]=[CH:29][C:19]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([S:1][C:2]4[CH:7]=[CH:6][C:9]([OH:12])=[CH:4][CH:3]=4)=[CH:24][CH:23]=3)=[O:21])=[CH:18][CH:17]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70344,4'-DichlorobenzophenoneHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 19387648HCID 19387648, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 4-mercaptophenol (50g, 0.317 mol for 80% purity), anhydrous potassium carbonate (46.9 9, g. 0.34 mol) and 150 mL of DMF was stirred and heated under nitrogen at 110°-120° C. for 90 min. The mixture was cooled to 80° C., a suspension of 4,4'-dichloro-benzophenone (40.1 g, 0.16 mol) in 100 mL DMF was added over 5 min and the mixture was stirred and heated under reflux for 4 h. After cooling to room temperature, there was added 400 mL of water and enough conc. HCl to adjust the pH to ca. 2. After stirring for 1 h, the pale yellow solid was filtered, washed with water and recrystallized from aqueous ethanol to afford 4,4'-bis(4-hydroxyphenylthio)benzo-phenone as pale yellow microcrystals, 59 g (86% yield), mp 219°-221° C. 1H NMR (DMSO-d6) was consistent with the structure with a sharp singlet for OH at δ 10.02 and four sets of doublets for the aromatic protons ranging from δ 7.61 to 6.99.

Workup

  1. temperatureheated under nitrogen at 110°-120° C. for 90 min
  2. additionwas added over 5 min
  3. stirringthe mixture was stirred
  4. temperatureheated
  5. temperatureunder reflux for 4 h
  6. temperatureAfter cooling to room temperature
  7. stirringAfter stirring for 1 h
  8. filtrationthe pale yellow solid was filtered
  9. washwashed with water
  10. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-4748d0991efa4d3ab69ba93b52fc4181
Source dataset
uspto-grants-1993_05
Patent number
US05208299

Linked notes

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