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Hydrochloric Acid → 1-Biphenyl-4-yl-propan-2-one

HRID 1956061
ノート
印刷プレビュー

反応式

HRID 1956061 の反応式
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.[CH2:17](OCC)C.CO.Cl>S(Cl)(Cl)=O.[Li].[Cu]>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH:3][C:4]([CH2:7][C:8](=[O:10])[CH3:17])=[CH:5][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl Ether2 回HCID 3332Felbinac

生成物 1

HCID 2193711-Biphenyl-4-yl-propan-2-one収率 96%

試薬・触媒・溶媒 2

HCID 57428120Copper;lithium触媒
HCID 24386
Thionyl Chloride
溶媒

反応条件

温度
80 °C

実験手順

10.5 g of 4-biphenylylacetic acid was dissolved in 50 ml of thionyl chloride, and the solution was heated at 80° C. for 3 hours. Then, excess thionyl chloride was distilled off under reduced pressure. Benzene was added to the residue, and the solvent was again distilled off. This operation was repeated again. Then, the formed acid chloride was dissolved in 100 ml of ethyl ether. Separately, 23.7 g of cuprous iodide was suspended in 50 ml of ethyl ether, and 166 ml of a 1.5M methyllithiumethyl ether solution was added thereto with stirring under cooling with ice to obtain a uniform solution. This solution was dropwise added to the ethyl ether solution of the acid chloride obtained by the above reaction under a nitrogen atmosphere while stirring and cooling to -70° C. After completion of the dropwise addition, the mixture was stirred at the same temperature for further one hour. Then, methanol was added thereto to decompose the excess copper lithium reagent. Ethyl ether and 2N hydrochloric acid were added to the reaction solution. After removing the formed insoluble matters by filtration, the filtrate was subjected to liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure to obtain 9.93 g (yield: 96%) of the above-identified compound as colorless oily substance.

後処理

  1. distillationThen, excess thionyl chloride was distilled off under reduced pressure
  2. additionBenzene was added to the residue
  3. distillationthe solvent was again distilled off
  4. dissolutionThen, the formed acid chloride was dissolved in 100 ml of ethyl ether
  5. addition166 ml of a 1.5M methyllithiumethyl ether solution was added
  6. temperatureunder cooling with ice
  7. customto obtain a uniform solution
  8. customobtained by the above reaction under a nitrogen atmosphere
  9. stirringwhile stirring
  10. temperaturecooling to -70° C
  11. additionAfter completion of the dropwise addition
  12. stirringthe mixture was stirred at the same temperature for further one hour
  13. customAfter removing the formed insoluble matters
  14. filtrationby filtration
  15. customthe filtrate was subjected to liquid separation
  16. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  17. dry with materialdried over anhydrous magnesium sulfate
  18. customThe drying agent was separated by filtration
  19. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-83086c2f7df64df897aed7c33493fea0
出典データセット
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05777150

反応ノート

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