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

HRID 1380346

Reaction equation

HRID 1380346 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 via 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. customthe reaction via NMR the reaction
  2. filtrationFilter off the catalysts
  3. washwash with methylene chloride
  4. customevaporate

Sources & evidence

ORD record
ord-413af3631eaf47fdb58ab7913b111ccb
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Linked notes

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