Quinoline → 3,7,11-Trimethyldodeca-1,6,10-trien-3-ol

HRID 436883Notes

Reaction equation

HRID 436883 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][C:12]([CH3:26])=[CH:13][CH2:14][CH2:15]/[C:16](/[CH3:25])=[CH:17]/[CH2:18][CH2:19][C:20]([OH:24])([C:22]#[CH:23])[CH3:21]>[Pd].[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCCCCC>[OH:24][C:20]([CH2:19][CH2:18][CH:17]=[C:16]([CH2:15][CH2:14][CH:13]=[C:12]([CH3:26])[CH3:11])[CH3:25])([CH:22]=[CH2:23])[CH3:21]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 53658233,7,11-Trimethyldodeca-6,10-dien-1-yn-3-ol

Product 1

HCID 88883,7,11-Trimethyldodeca-1,6,10-trien-3-olYield 90.6%

Reagents, catalysts & solvents 2

HCID 131710810Pd Lindlar catalystCatalystHCID 8058HexaneSolvent

Procedure

Further, 0.5 ml of quinoline and 20 g of 0.25% Pd-Lindlar catalyst was added in a solution of 1,280 g of the said dehydronerolidol in 2,000 ml of n-hexane and the mixture was hydrogenated at room temperature and normal pressure. After post-treatment, the reaction mixture was subjected to vacuum distillation to give 1,170 g of nerolidol having b.p. 105° - 110° C. (0.5 mmHg).

Workup

  1. customwas hydrogenated at room temperature
  2. distillationAfter post-treatment, the reaction mixture was subjected to vacuum distillation

Sources & evidence

ORD record
ord-7d45f6fc1930445095d4e703d19bd850
Source dataset
uspto-grants-1977_06
Patent number
US04028385

Reaction notes

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