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

HRID 437926Notes

Reaction equation

HRID 437926 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9][C:10]([OH:14])([C:12]#[CH:13])[CH3:11].[Cl-].[NH4+].[OH2:19].O=O>C(O)C>[CH3:16][C:2](=[CH:3][CH2:4][CH2:5][C:6]([CH3:15])=[CH:7][CH2:8][CH2:9][C:10]([CH3:11])([OH:19])[C:12]#[C:13][C:13]#[C:12][C:10]([CH3:11])([OH:14])[CH2:9][CH2:8][CH:7]=[C:6]([CH3:15])[CH2:5][CH2:4][CH:3]=[C:2]([CH3:16])[CH3:1])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 977OxygenHCID 25517Ammonium ChlorideHCID 53658233,7,11-Trimethyldodeca-6,10-dien-1-yn-3-ol

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

A 5 l-capacity, 3-neck, round-bottom flask was charged with 114.7 g of dehydronerolidol, 305.9 g of ammonium chloride, 191.2 g of cuprous chloride, 765 ml of water and 765 ml of ethyl alcohol, and the mixture was agitated at room temperature for 18 hours while blowing oxygen thereinto. After completion of the reaction, none of the starting reactants were left. The reaction mixture was separated with a centrifuge, and the mother solution was extracted with benzene. Benzene and ethyl alcohol were removed from the organic layer by distillation, and the residue was dissolved in benzene and washed with water. The resulting benzene solution was dried with anhydrous calcium sulfate and the solids were removed from the dried solution by filtration. Distillation of benzene from the benzene solution gave 107.8 g of a viscous liquid of 2,6,10,15,19,23-hexamethyltetracosa-2,6,18,22-tetraene-11,13-diyne-10,15-diol.

Workup

  1. customAfter completion of the reaction, none of the starting reactants
  2. waitwere left
  3. customThe reaction mixture was separated with a centrifuge
  4. extractionthe mother solution was extracted with benzene
  5. customBenzene and ethyl alcohol were removed from the organic layer by distillation
  6. dissolutionthe residue was dissolved in benzene
  7. washwashed with water
  8. dry with materialThe resulting benzene solution was dried with anhydrous calcium sulfate
  9. customthe solids were removed from the dried solution by filtration
  10. distillationDistillation of benzene from the benzene solution

Sources & evidence

ORD record
ord-1f461d6852394b0aadc9a8affd27b610
Source dataset
uspto-grants-1977_06
Patent number
US04032588

Reaction notes

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