Thiophenol → 4-(Phenylsulfanyl)butan-1-ol

HRID 745178

反応式

HRID 745178 の反応式
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:9][CH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(Cl)(Cl)Cl>[C:1]1([S:7][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 135694-Chloro-1-butanol

生成物 1

HCID 2837984-(Phenylsulfanyl)butan-1-ol収率 57.8%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of thiophenol (121.2 g, 1.10 mole), 4-chloro-1-butanol (100.0 g, 0.921 mole), and potassium carbonate (138.2 g, 1.0 mole) was heated overnight at gentle reflux in dimethoxyethane. The reaction mixture was filtered and solvent removed by rotary evaporator. The residue obtained was dissolved in chloroform and extracted with 10% sodium hydroxide. The chloroform layer was dried, filtered, and solvent removed to give an oil which crystallized to a white solid. The solid was vacuum distilled at 134°-140° C./0.55 mm. A six-gram sample of the distilled oil was subjected to flash chromatography on silica gel using ethyl acetate-hexanes for elution. This gave a clear oil which was dried at 80° C. overnight in vacuo. The process produced 5.2 g (57.8%) of clear oil.

後処理

  1. temperaturewas heated overnight
  2. filtrationThe reaction mixture was filtered
  3. customsolvent removed by rotary evaporator
  4. customThe residue obtained
  5. extractionextracted with 10% sodium hydroxide
  6. dry with materialThe chloroform layer was dried
  7. filtrationfiltered
  8. customsolvent removed
  9. customto give an oil which
  10. customcrystallized to a white solid
  11. distillationdistilled at 134°-140° C./0.55 mm
  12. washfor elution
  13. customThis gave a clear oil which
  14. customwas dried at 80° C. overnight in vacuo

出典と根拠

ORDレコード
ord-7d6d7d5736164329ac916bf8f3b0df43
出典データセット
uspto-grants-1986_07
特許番号
US04597902

関連ノート

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