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

HRID 1183868Notes

Reaction equation

HRID 1183868 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

150 ml concentrated sulfuric acid was added to 16 g (0.103 mol) thiosalicylic acid. 60 g (0.44 mol) phenol was added portion wise. The temperature rose to 50° C. during the addition. The mixture was allowed to cool down to room temperature and stirred for 30 minutes at room temperature. The mixture was heated to 80° C. for 48 hours. The mixture was allowed to cool down to room temperature and carefully added over one hour to 3 l water at 75° C. The mixture was stirred for an additional hour at 60° C. and allowed to cool down to room temperature. 2-hydroxy-9H-thioxanthen-9-one was isolated by filtration and dried. 12.9 g of 2-hydroxy-9H-thioxanthen-9-one (55%) was isolated. 2-hydroxy-9H-thioxanthen-9-one was sufficiently pure to be used without further purification.

Workup

  1. additionThe temperature rose to 50° C. during the addition
  2. temperatureThe mixture was heated to 80° C. for 48 hours
  3. temperatureto cool down to room temperature
  4. stirringThe mixture was stirred for an additional hour at 60° C.
  5. temperatureto cool down to room temperature

Sources & evidence

ORD record
ord-a3997760cc5345998a96038dc5ebdcdb
Source dataset
uspto-grants-2014_03
Patent number
US08664431B2

Reaction notes

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