Pyridine → HCID 54073489, compound

HRID 1606687Notes

Reaction equation

HRID 1606687 reaction equation
[OH:1][C:2]([CH3:13])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]#[CH:4].N1C=CC=CC=1>[H][H].[Pd]>[OH:1][C:2]([CH3:13])([CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:3]=[CH2:4]

Participants

5

Reactant 2

HCID 1049PyridineHCID 21544183HCID 21544183, compound

Product 1

HCID 54073489HCID 54073489, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 20.0 g. of 3-hydroxy-3-methyl-undec-1-yne, 200 ml. of pyridine, and 500 mg. of 5% palladium on barium sulfate is shaken in hydrogen at an initial pressure of 45 lb./sq. in. The hydrogenation is stopped when the calculated amount for one mole uptake per mole of compound has been absorbed. The mixture is poured into water and extracted with ether. The ether extract is washed with water, dilute hydrochloric acid, aqueous sodium bicarbonate, dried, and evaporated under reduced pressure to give a residue which is distilled through a Vigreaux column to give a distillate comprising 3-hydroxy-3-methyl-1,5-undecadiene.

Workup

  1. additionA mixture of 20.0 g
  2. customhas been absorbed
  3. additionThe mixture is poured into water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with water, dilute hydrochloric acid, aqueous sodium bicarbonate
  7. customdried
  8. customevaporated under reduced pressure
  9. customto give a residue which
  10. distillationis distilled through a Vigreaux column

Sources & evidence

ORD record
ord-a9df5bc168bd4795850af8c178c9e74b
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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