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

HRID 1789456

Reaktionsgleichung

Reaktionsgleichung von HRID 1789456
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b179caa1edde4d7db85b74b59893ce31
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689341

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