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

HRID 42735

Reaction equation

HRID 42735 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].S(=O)(=O)(O)O.[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:4][C:3]3[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1](=[O:10])[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

16 g (103 mmol) thiosalicylic acid was slowly added to 150 mL concentrated sulfuric acid. The mixture is stirred for 5 minutes and 60 g (440 mmol) phenol was added over 30 minutes. The temperature rose to 60° C. The reaction was allowed to continue for 2 hours at 80° C. The reaction was allowed to cool down to room temperature and was added slowly to 31 boiling water. The mixture was kept at the boiling point for 5 minutes. The mixture was allowed to cool down to room temperature. The precipitated 2-hydroxy-thioxanthen-9-on was isolated by filtration and dried. 14.1 g (63%) of 2-hydroxy-thioxanthen-9-on was isolated (m.p. 232-241° C.)

Workup

  1. customrose to 60° C
  2. waitto continue for 2 hours at 80° C
  3. waitThe mixture was kept at the boiling point for 5 minutes
  4. temperatureto cool down to room temperature

Sources & evidence

ORD record
ord-8b29f5dd6897410091109be9c60f3e7e
Source dataset
uspto-grants-2013_09
Patent number
US08536217B2

Linked notes

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