Phloroglucinol → 2-Methoxy-1-(2,4,6-trihydroxyphenyl)ethanone

HRID 1506834

反応式

HRID 1506834 の反応式
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:10][O:11][CH2:12][C:13]#N.C([O:17]CC)C>[Cl-].[Zn+2].[Cl-]>[CH3:10][O:11][CH2:12][C:13]([C:9]1[C:1]([OH:2])=[CH:3][C:4]([OH:5])=[CH:6][C:7]=1[OH:8])=[O:17]

参加物

5

反応物 3

HCID 359PhloroglucinolHCID 3283Diethyl EtherHCID 74442Methoxyacetonitrile

生成物 1

HCID 6434002-Methoxy-1-(2,4,6-trihydroxyphenyl)ethanone収率 81%

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

実験手順

Phloroglucinol (35.1 g, 279 mmol) was dissolved into ethyl ether (500 mL) solution, followed by zinc chloride (8 g, 59 mmol) and 2-methoxy acetonitrile (18 g, 253 mmol) added in the solution under ice water bath condition. Dry HCl gas was bubbled into the reaction mixture, vigorously stirring for 5 hours, and precipitate was formed. The precipitate was filtered and collected, followed by dissolved into water and refluxed for 3 hours. After cooling, pink precipitate was collected, and desired white compound can be obtained after recrystallization with water. (45 g, yield 81%) 1HNMR (400 MHz, DMSO-d6): δ=12.14 (s, 2H), 10.41 (s, 1H), 5.79 (s, 2H), 4.56 (s, 2H), 3.32 (s, 3H).

後処理

  1. additionadded in the solution under ice water bath condition
  2. customDry HCl gas was bubbled into the reaction mixture
  3. customprecipitate was formed
  4. filtrationThe precipitate was filtered
  5. customcollected
  6. dissolutionby dissolved into water
  7. temperaturerefluxed for 3 hours
  8. temperatureAfter cooling
  9. custompink precipitate was collected
  10. customdesired white compound can be obtained
  11. customafter recrystallization with water

出典と根拠

ORDレコード
ord-3fe139a606c14a0d83c37aa1a17f3b1e
出典データセット
uspto-grants-2015_12
特許番号
US09221781B2

関連ノート

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