Sulfuric Acid → Methylthioxanthone

HRID 867190Notes

Reaction equation

HRID 867190 reaction equation
S(=O)(=O)(O)O.[SH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](O)=[O:10]>C1(C)C=CC=CC=1>[CH3:9][C:8]1[C:12]2[C:9](=[O:10])[C:8]3[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:6][C:13]=2[CH:14]=[CH:15][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54432-Mercaptobenzoic Acid

Product 1

HCID 15566316Methylthioxanthone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of concentrated sulphuric acid (300 ml) and toluene (46 ml), o-mercaptobenzoic acid (30 g) was added slowly. The mixture was stirred for 8 hrs. and allowed to stand for a further 10 hrs. After 1 hr. heating on the steam bath the dark red solution was cooled and poured on to ice. The gummy yellow precipitate was filtered off and triturated with 2N aqueous sodium hydroxide. The solid isomer-mixture was filtered off, washed with water, and dried at room temperature in vacuo, m.p. 107°-132° C.

Workup

  1. additionwas added slowly
  2. waitto stand for a further 10 hrs
  3. waitAfter 1 hr
  4. temperatureheating on the steam bath the dark red solution
  5. temperaturewas cooled
  6. additionpoured on to ice
  7. filtrationThe gummy yellow precipitate was filtered off
  8. customtriturated with 2N aqueous sodium hydroxide
  9. filtrationThe solid isomer-mixture was filtered off
  10. washwashed with water
  11. customdried at room temperature in vacuo, m.p. 107°-132° C.

Sources & evidence

ORD record
ord-5a3fa1c38dc04461bcad2c834211e721
Source dataset
uspto-grants-1978_07
Patent number
US04103015

Reaction notes

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