7,11-Hexadecadiyn-1-ol, 1-acetate → Gossyplure

HRID 1973169Notes

Reaction equation

HRID 1973169 reaction equation
[Al].[C:2]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH2:14][CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:4])[CH3:3].[H][H]>N1C2C(=CC=CC=2)C=CC=1.[Cu].[Pd].CCCCCC>[C:2]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH3:21])(=[O:4])[CH3:3]

Participants

8

Reactant 3

HCID 1128057,11-Hexadecadiyn-1-ol, 1-acetateHCID 5359268AluminumHCID 178418361HCID 178418361, compound

Product 1

HCID 5363265Gossyplure

Reagents, catalysts & solvents 4

HCID 7047QuinolineCatalystHCID 23938PalladiumCatalystHCID 23978CopperCatalystHCID 8058HexaneSolvent

Procedure

Into a 500 ml Parr hydrogenation flask fitted with an aluminum or copper cooling coil is placed 100 g of 7,11-hexadecadiynyl acetate, 100 ml hexane (olefin free), 1 g palladium on calcium carbonate (Lindlar catalyst) and 10 drops of synthetic quinoline. Hydrogenation is effected at 10- 20 psi and is complete when the theoretical amount of hydrogen for the partial reduction of two triple bonds is absorbed. During the hydrogenation the reaction temperature is maintained between 15°-25° to minimize cis-trans isomeration. The catalyst is then removed by filtration and the product isolated by distillation of the filtrate. bp 130°-132°/1 torr nD21 1.4592. Yield essentially quantitative. Based on IR analysis it is estimated that there is less than 5% of E isomers present.

Workup

  1. customis absorbed
  2. temperatureDuring the hydrogenation the reaction temperature is maintained between 15°-25°
  3. customThe catalyst is then removed by filtration
  4. customthe product isolated by distillation of the filtrate
  5. customYield essentially quantitative

Sources & evidence

ORD record
ord-02f7cbafa4304d789184a99e5ec43f03
Source dataset
uspto-grants-1976_12
Patent number
US03996270

Reaction notes

Loading…