Water → 2,6,10,15,19,23-Hexamethyltetracosa-2,6,18,22-tetraene-11,13-diyne-10,15-diol

HRID 596559Notes

Reaction equation

HRID 596559 reaction equation
[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:3]#[CH:4].[Cl-].[NH4+].[OH2:19].O=O>C(O)C>[CH3:14][C:12](=[CH:11][CH2:10][CH2:9][C:8]([CH3:15])=[CH:7][CH2:6][CH2:5][C:2]([CH3:1])([OH:19])[C:3]#[C:4][C:4]#[C:3][C:2]([CH3:1])([OH:16])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 977OxygenHCID 25517Ammonium ChlorideHCID 102805Dehydronerolidol

Product 1

HCID 538493542,6,10,15,19,23-Hexamethyltetracosa-2,6,18,22-tetraene-11,13-diyne-10,15-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 5-l. three-necked, and round-bottomed flask were placed 114.7 g of 3,7,11-trimethyldodeca-6,10-dien-l-yne-3-ol, 305.9 g of ammonium chloride, 765 ml of water and 76.5 ml of ethyl alcohol and the mixture was stirred at a room temperature by passing oxygen for 18 hours. After completion of the reaction, no starting material remained. The reaction mixture was centrifuged and was extracted with benzene. The organic layer was distilled off to remove benzene and ethyl alcohol. The residue was dissolved in benzene and washed with water. The benzene solution was dried over anhydrous calcium sulfate and the solid material was filtered off. The benzene solution thus obtained was distilled off to give 107.8 g of 2,6,10,15,19,23-hexamethyltetracosa-2,6,18,22-tetraene-11,13-diyne-10,15-diol as viscous liquid. A 3 g of this substance was further dissolved in 10 ml of benzene, treated with active carbon and purified by distilling the benzene.

Workup

  1. customthree-necked, and round-bottomed flask were placed
  2. customfor 18 hours
  3. customAfter completion of the reaction
  4. extractionwas extracted with benzene
  5. distillationThe organic layer was distilled off
  6. customto remove benzene and ethyl alcohol
  7. dissolutionThe residue was dissolved in benzene
  8. washwashed with water
  9. dry with materialThe benzene solution was dried over anhydrous calcium sulfate
  10. filtrationthe solid material was filtered off
  11. customThe benzene solution thus obtained
  12. distillationwas distilled off

Sources & evidence

ORD record
ord-bdc3351d21144e3bad954ec0100e07f3
Source dataset
uspto-grants-1977_03
Patent number
US04011277

Reaction notes

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