3,6,7-Trimethyloct-6-en-1-yn-3-ol → HCID 117871987, compound

HRID 55913Notes

Reaction equation

HRID 55913 reaction equation
[CH3:1][C:2]([OH:12])([CH2:5][CH2:6][C:7]([CH3:11])=[C:8]([CH3:10])[CH3:9])[C:3]#[CH:4].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:1][C:2]([OH:12])([CH2:5][CH2:6][C:7]([CH3:11])=[C:8]([CH3:10])[CH3:9])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1036603,6,7-Trimethyloct-6-en-1-yn-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 117871987HCID 117871987, compound

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Conditions

Temperature
45 °C

Procedure

383.0 g of 3,6,7-trimethyl-6-octen-1-in-3-ol and 0.3 g of Lindlar catalyst (5% Pd+3.5% Pb on CaCO3) are put in an autoclave and heated under nitrogen to a temperature of 45° C. Nitrogen is exchanged by hydrogen (H2) and the reaction mixture put at an absolute pressure of 2 bar. After the calculated amount of hydrogen has been consumed the reaction mixture is filtered and distilled (2 mbar, 115° C.) to obtain 3,6,7-trimethyl-6-octen-3-ol (=compound of formula (Ia)).

Workup

  1. customAfter the calculated amount of hydrogen has been consumed the reaction mixture
  2. filtrationis filtered
  3. distillationdistilled (2 mbar, 115° C.)

Sources & evidence

ORD record
ord-944957ec93d547bca8026a8cecdec329
Source dataset
uspto-grants-2016_09
Patent number
US09434676B2

Reaction notes

Loading…