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

HRID 1789457

Reaction equation

HRID 1789457 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-93abc6b367ac4c85828867dcc8b49366
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Linked notes

Loading…