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Phloroglucinol → 1,3-dihydroxy-9H-thioxanthen-9-one

HRID 83097
Notes
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Reaction equation

HRID 83097 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15](O)(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[SH:18].[C:25]1([CH:33]=[C:31]([OH:32])[CH:30]=[C:28]([OH:29])[CH:27]=1)O>CS(O)(=O)=O>[OH:32][C:31]1[C:33]2[C:15](=[O:23])[C:16]3[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:18][C:25]=2[CH:27]=[C:28]([OH:29])[CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 359PhloroglucinolHCID 54432-Mercaptobenzoic AcidHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 112880161,3-dihydroxy-9H-thioxanthen-9-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of phosphorous pentoxide (3.71 g, 26.15 mmol) and methane sulfonic acid (27.05 mL, 0.42 mmol) was stirred at 90° C. for about one hour until a clear solution was obtained. To the reaction solution were added thiosalicylic acid (1.04 g, 6.76 mmol) and phloroglucinol (1.02 g, 8.11 mmol), followed by stirring at 70° C. for 10 minutes. After the reaction was completed, the reaction mixture was poured in 1 L of ice water. The resulting precipitate was allowed to stand at 4° C. overnight, combined, washed with water, and then dried under reduced pressure to give an orange solid compound. This compound was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v)) to give a yellow solid compound (1.14 g, 51.1%).

Workup

  1. customwas obtained
  2. stirringby stirring at 70° C. for 10 minutes
  3. waitto stand at 4° C. overnight
  4. washwashed with water
  5. customdried under reduced pressure
  6. customto give an orange solid compound
  7. customThis compound was separated
  8. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v))

Sources & evidence

ORD record
ord-1b328ce19ee946a4a8db17dbdac99565
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846749B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes