Hydrochloric Acid → 3-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

HRID 553223ノート

反応式

HRID 553223 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-:13].[CH2:14]([N+](C)(C)C)[C:15]1[CH:20]=CC=CC=1.C(#N)C=C.Cl.S(=O)(=O)(O)O.[OH2:35]>C(O)CC.C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:14][CH2:15][C:20]([OH:35])=[O:13])=[CH:9][C:4]=2[CH:3]=[CH:2]1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

生成物 1

HCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 1140Toluene溶媒

反応条件

温度
15 °C

実験手順

To toluene (50 mL) suspension of 50.0 g of 2-(1-benzothiophen-5-yl)ethanol was added 2.35 g of 40% (w/w) benzyltrimethylammonium hydroxide aqueous solution, and dropwise added 17.9 g of acrylonitrile at 8 to 15° C., which was then stirred at 10 to 20° C. for 1.5 hours. To this reaction mixture were added 1.25 mL of hydrochloric acid, 100 mL of propanol and 5.05 g of water. Thereto was dropwise added 55.0 g of sulfuric acid, which was then refluxed for 6 hours. After cooling, to the reaction mixture was added 100 mL of water. The organic layer was separated. Thereto was added 50 mL of methanol and dropwise added water (50 mL) solution of 31.5 g of potassium hydroxide, which was then stirred at room temperature for 1.5 hours. To this reaction mixture were added 75 mL of toluene and 75 mL of water. The aqueous layer was separated, thereto was added 100 mL of toluene, the pH was adjusted to 0.9 with 6 mol/L hydrochloric acid, and the organic layer was separated. After the solvent was distilled off under reduced pressure, thereto were added 50 mL of toluene and 125 mL of cyclohexane. The precipitate was collected by filtration to provide 59.6 g of 3-(2-(1-benzothiophen-5-yl)ethoxy)propionic acid as white solid form.

後処理

  1. temperaturewas then refluxed for 6 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. customThe organic layer was separated
  4. additionThereto was added 50 mL of methanol and dropwise added water (50 mL) solution of 31.5 g of potassium hydroxide, which
  5. stirringwas then stirred at room temperature for 1.5 hours
  6. additionTo this reaction mixture were added 75 mL of toluene and 75 mL of water
  7. customThe aqueous layer was separated
  8. additionwas added 100 mL of toluene
  9. customthe organic layer was separated
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. additionwere added 50 mL of toluene and 125 mL of cyclohexane
  12. filtrationThe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-c11e96da5113419c98c626138ef14353
出典データセット
uspto-grants-2011_05
特許番号
US07951963B2

反応ノート

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