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

HRID 464028

反応式

HRID 464028 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](CC#C)=[CH:4][CH:3]=1.[C:11](=[O:13])=O.[CH3:14][C:15]([CH3:17])=O.C([Li])CCC.C=O.[Cl-].[Na+]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:11]([OH:13])[C:14]#[C:15][CH3:17])=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 136602551-Chloro-4-(2-propyn-1-yl)benzeneHCID 18522661Acetone cardice2 回HCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Dissolve 150.6 g (1.00 mole) of 1-chloro-4-(2-propynyl)benzene in 600 ml of anhydrous ether under N2 atmosphere with stirring at dry ice/acetone temperature. Add dropwise a solution of 400 ml of n-butyllithium (2.5M in hexane) (1.00 mole). Stir for an additional 30 minutes after completion of addition. Add 31 g (1.00 mole) of paraformaldehyde. Stir the mixture at dry ice/acetone temperature for 1 hour, and allow to warm to room temperature. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride). At the completion of the reaction, add 400 ml of saturated aqueous sodium chloride, separate layers, and extract aqueous layer with ether (2×100 ml). Wash the combined ether solutions with water, dry over magnesium sulfate and evaporate. Triturate the oil residue with petroleum ether to provide the title compound.

後処理

  1. additionafter completion of addition
  2. customthe progress of the reaction by thin-layer chromatography on silica gel (methylene chloride)
  3. customAt the completion of the reaction
  4. customseparate layers
  5. extractionextract aqueous layer with ether (2×100 ml)
  6. washWash the combined ether solutions with water
  7. dry with materialdry over magnesium sulfate
  8. customevaporate
  9. customTriturate the oil residue with petroleum ether

出典と根拠

ORDレコード
ord-784f89dba3af4af7aed86a23f7a5bf5b
出典データセット
uspto-grants-1985_10
特許番号
US04545995

関連ノート

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