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

HRID 464028

Reaction equation

HRID 464028 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-784f89dba3af4af7aed86a23f7a5bf5b
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Linked notes

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