Formaldehyde → 1-(4-Chlorophenyl)-2-butyn-1-ol

HRID 65234

反応式

HRID 65234 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5](CC#C)=[CH:4][CH:3]=1.[CH2:11]([Li])[CH2:12][CH2:13]C.[CH2:16]=[O:17].[Cl-:18].[Na+]>CCOCC.CCCCCC>[Cl:18][C:2]1[CH:7]=[CH:6][C:5]([CH:16]([OH:17])[C:11]#[C:12][CH3:13])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 136602551-Chloro-4-(2-propyn-1-yl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 201883391-(4-Chlorophenyl)-2-butyn-1-ol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

Under nitrogen and with cooling, to a solution of 150.6 g (1.0 mole) 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether, add dropwise 400 ml of 2.5M n-butyllithium (1.0 mole) in hexane. When addition is complete, stir a further 30 minutes and under N2 add 31 g of para-formaldehyde. Stir the mixture in a dry ice/acetone bath for 1 hour. Allow to warm to room temperature and then allow to reflux. When the reaction is complete, add 400 ml of saturated aqueous sodium chloride. Separate the layers and extract the aqueous layer with ether. Wash the combined ether solution, wash with water and dry over magnesium sulfate. Evaporate off the ether, dissolve the residue in hot cyclohexane which yielded crystalline material the title compound.

後処理

  1. additionWhen addition
  2. stirringStir the mixture in a dry ice/acetone bath for 1 hour
  3. temperatureto reflux
  4. customSeparate the layers
  5. extractionextract the aqueous layer with ether
  6. washWash the combined ether solution
  7. washwash with water
  8. dry with materialdry over magnesium sulfate
  9. customEvaporate off the ether
  10. dissolutiondissolve the residue in hot cyclohexane which

出典と根拠

ORDレコード
ord-20fd872bfe264e6fb36a86a1a04070a7
出典データセット
uspto-grants-1986_09
特許番号
US04613609

関連ノート

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