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

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

Participants

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

customwas obtained
stirringby stirring at 70° C. for 10 minutes
waitto stand at 4° C. overnight
washwashed with water
customdried under reduced pressure
customto give an orange solid compound
customThis compound was separated
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

Linked notes

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