Ammonia → 3,7,11-Trimethyldodeca-6,10-dien-1-yn-3-ol

HRID 437925Notes

Reaction equation

HRID 437925 reaction equation
N.[Na].[CH:3]#[CH:4].[CH2:5]([CH2:15][C:16](=[O:18])[CH3:17])/[CH:6]=[C:7](/[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])\[CH3:8].[Cl-].[NH4+]>>[CH3:14][C:12]([CH3:13])=[CH:11][CH2:10][CH2:9]/[C:7](/[CH3:8])=[CH:6]/[CH2:5][CH2:15][C:16]([OH:18])([C:3]#[CH:4])[CH3:17]

Participants

6

Reactant 5

HCID 222Ammonia3×HCID 6326AcetyleneHCID 25517Ammonium ChlorideHCID 1549778GeranylacetoneHCID 5360545Sodium

Product 1

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

Procedure

A 2 l-capacity, 3-neck, round-bottom flask was charged with 1000 ml of liquid ammonia and 11.5 g of metallic sodium was added thereto. Acetylene gas was blown into the flask, and when the color of the liquid ammonia solution changed from bluish green to white, 97 g of geranyl acetone was added to the solution and the reaction was conducted under reflux for 4 hours. After completion of the reaction, 54 g of ammonium chloride was added to the reaction mixture and liquid ammonia was removed by distillation. Then, 500 ml of ethyl ether and 500 ml of water were added to the residue to cause phase separation. The organic layer was washed with water and distillation of the ether gave 108 g of dehydronerolidol.

Workup

  1. additionwas added
  2. additionwas added to the solution
  3. temperatureunder reflux for 4 hours
  4. customwas removed by distillation
  5. additionThen, 500 ml of ethyl ether and 500 ml of water were added to the residue
  6. customphase separation
  7. washThe organic layer was washed with water and distillation of the ether

Sources & evidence

ORD record
ord-12bae022a5d646c4add8c134c630a17c
Source dataset
uspto-grants-1977_06
Patent number
US04032588

Reaction notes

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