3,6-Dimethyl-oct-1-yn-4-en-3-ol → 3,6-Dimethyl-octa-1,4-dien-3-ol

HRID 68015Notes

Reaction equation

HRID 68015 reaction equation
[CH3:1][C:2]([OH:11])([CH:5]=[CH:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:3]#[CH:4].[H][H]>CO.[Pd].[Zn]>[CH3:1][C:2]([OH:11])([CH:5]=[CH:6][CH:7]([CH3:10])[CH2:8][CH3:9])[CH:3]=[CH2:4]

Participants

6

Reactant 2

HCID 536333433,6-Dimethyl-oct-1-yn-4-en-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 536532163,6-Dimethyl-octa-1,4-dien-3-olYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

154 g (1 mole) of 3,6-dimethyl-oct-1-yn-4-en-3-ol are dissolved in 100 ml of methanol, 1 g of an 0.1% strength palladium/calcium carbonate catalyst, which has been poisoned with zinc ions, is added, and hydrogen is passed in at 15°-20° C. under atmospheric pressure. After 6 hours, the mixture is worked up similarly to Example 2. 145 g of 3,6-dimethyl-octa-1,4-dien-3-ol, of boiling point 38°-39° C./0.01 mbar and nD25 =1.4502, are obtained. This corresponds to a yield of 93% of theory.

Workup

  1. additionis added
  2. customis passed in at 15°-20° C. under atmospheric pressure

Sources & evidence

ORD record
ord-05648ad04d564e988f428848e8d7dda0
Source dataset
uspto-grants-1982_08
Patent number
US04347388

Reaction notes

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