Phenol → 2-Hydroxy-9H-thioxanthen-9-one

HRID 1649563Notes

Reaction equation

HRID 1649563 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:15])(=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[SH:9].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[OH:22][C:16]1[CH:21]=[CH:20][C:19]2[S:9][C:8]3[C:7](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6](=[O:15])[C:18]=2[CH:17]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric AcidHCID 54432-Mercaptobenzoic Acid

Product 1

HCID 97945682-Hydroxy-9H-thioxanthen-9-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulphuric acid (300 ml) was slowly added to thiosalicylic acid (30.9 g) and the mixture was stirred for 5 minutes to ensure thorough mixing. Phenol (94 g) was added slowly to the stirred mixture over a period of 30 minutes. After the addition, the mixture was stirred at room temperature for 1 hour, then at 80° C. for two hours, after which it was left to stand at room temperature overnight. The resulting mixture was poured carefully with stirring into 10 times its volume of boiling water which was then boiled for a further 5 minutes. The solution was cooled and filtered. The residue was recrystallised from acetone to give 2-hydroxythioxanthone as a yellow product.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. waitat 80° C. for two hours
  4. waitafter which it was left
  5. waitto stand at room temperature overnight
  6. additionThe resulting mixture was poured carefully
  7. waitwas then boiled for a further 5 minutes
  8. temperatureThe solution was cooled
  9. filtrationfiltered
  10. customThe residue was recrystallised from acetone

Sources & evidence

ORD record
ord-8bda65a8aaa343c8afd58134420e50d6
Source dataset
uspto-grants-1983_11
Patent number
US04418138

Reaction notes

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