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

HRID 83097

反応式

HRID 83097 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 112880161,3-dihydroxy-9H-thioxanthen-9-one収率 69%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid触媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-1b328ce19ee946a4a8db17dbdac99565
出典データセット
uspto-grants-2014_09
特許番号
US08846749B2

関連ノート

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