Pyridine → 19-Chloro-6-methylnonadeca-6,9,12-triene

HRID 1606677Notes

Reaction equation

HRID 1606677 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N1C=CC=CC=1.[H][H]>[Pd].O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 536494751-Chloro-14-methyl-nonadeca-7,10-diyn-13-eneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 5443945819-Chloro-6-methylnonadeca-6,9,12-triene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 11.0 g. of 1-chloro-14-methyl-nonadeca-7,10-diyn-13-ene, 1.5 g. of 5% palladium on barium sulfate, and 80 ml. of pyridine was shaken in a Parr rocker under 40 lb. of hydrogen pressure for about 1.3 hrs., at which time two moles of hydrogen had been absorbed. The reaction mixture was then poured into water and extracted with ether. The extract was washed with water, dilute hydrochloric acid, saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated leaving a residue comprising 1-chloro-14-methyl-7,10,13-nonadecatriene. The residue was distilled in a rocking short-path distillation apparatus, collecting 7.6 g. of a mixture comprising 1-chloro-14-methyl-7,10,13-nonadecatriene at a bath temperature of 180°C. and a pressure of 0.005 mm.

Workup

  1. additionA mixture of 11.0 g
  2. extractionextracted with ether
  3. washThe extract was washed with water, dilute hydrochloric acid, saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-604faddc693448ffa6a8516f21b8fb9c
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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