1-Chloro-10,14-dimethylnonadeca-10,13-dien-7-yne → 1-Chloro-10,14-dimethylnonadeca-7,10,13-triene

HRID 1606682Notes

Reaction equation

HRID 1606682 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:10][C:11]([CH3:22])=[CH:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[H][H]>S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.N1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][C:11]([CH3:22])=[CH:12][CH2:13][CH:14]=[C:15]([CH3:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 536713201-Chloro-10,14-dimethylnonadeca-10,13-dien-7-yneHCID 178418361HCID 178418361, compound

Product 1

HCID 536620151-Chloro-10,14-dimethylnonadeca-7,10,13-triene

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 5.0 g. of 1-chloro-10,14-dimethylnonadeca-10,13-dien-7-yne 500 mg. of 5% palladium-barium sulfate catalyst and 40 ml. of pyridine is shaken under hydrogen for about 2 hrs. (until the uptake of hydrogen practically ceases). The mixture is then filtered, diluted with water, and extracted with ether. The ether extract is washed with water, dilute hydrochloric acid, and aqueous sodium bicarbonate, then is dried over sodium sulfate and evaporated to leave a residue comprising 1-chloro-10,14-dimethylnonadeca-7,10,13-triene.

Workup

  1. additionA mixture of 5.0 g
  2. filtrationThe mixture is then filtered
  3. additiondiluted with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with water, dilute hydrochloric acid, and aqueous sodium bicarbonate
  7. dry with materialis dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-bdf088d3f2e94ed282f39eb91d3101d4
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

Loading…