Sulfuric Acid → 2-Hydroxy-3,4-dimethyl-9H-thioxanthen-9-one

HRID 1462230Notes

Reaction equation

HRID 1462230 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].[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[OH:24]>O>[OH:24][C:18]1[C:17]([CH3:16])=[C:22]([CH3:23])[C:21]2[S:9][C:8]3[C:7](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6](=[O:15])[C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 54432-Mercaptobenzoic AcidHCID 106872,3-Dimethylphenol

Product 1

HCID 135937022-Hydroxy-3,4-dimethyl-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. To the stirred mixture was added slowly over a period of 30 minutes 2,3-dimethyl-phenol (138 g). After the addition, the mixture was stirred at room temperature for 1 hour, and then at 80° C. for 2 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 after which it was boiled for a further five minutes, cooled, and filtered. The residue was recrystallised from acetone to give 2-hydroxy-3,4-dimethyl-thioxanthone 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 2 hours
  4. waitafter which it was left
  5. waitto stand at room temperature overnight
  6. additionThe resulting mixture was poured carefully
  7. waitwas boiled for a further five minutes
  8. temperaturecooled
  9. filtrationfiltered
  10. customThe residue was recrystallised from acetone

Sources & evidence

ORD record
ord-44859123e4114ca8971d628ceed3f15a
Source dataset
uspto-grants-1984_07
Patent number
US04459416

Reaction notes

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