1-(4-Chlorophenyl)-2-butyn-1-ol → (Z)-1-(4-chlorophenyl)-2-buten-1-ol

HRID 65235

Reaction equation

HRID 65235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])/[CH:9]=[CH:10]\[CH3:11])=[CH:6][CH:7]=1

Participants

3

Reactant 1

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

Product 1

HCID 67901371(Z)-1-(4-chlorophenyl)-2-buten-1-ol

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

Under nitrogen, hydrogenate a mixture of 10 g (0.055 mole) of 1-(4-chlorophenyl)-2-butyn-1-ol and 0.6 g Lindlar catalyst. Following the reaction vic NMR the reaction is complete in about two days. The hydrogenation is stopped and the reaction stirred under N2 at room temperature overnight. Filter off the catalysts, wash with methylene chloride combine the filtrate and evaporate to yield the title compound.

Workup

  1. filtrationFilter off the catalysts
  2. washwash with methylene chloride
  3. customevaporate

Sources & evidence

ORD record
ord-1ba35f007e7240af90d3407e16dabfe8
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Linked notes

Loading…