N,N,N',N'-Tetramethylethylenediamine → 2,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol

HRID 596560Notes

Reaction equation

HRID 596560 reaction equation
[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]#[CH:4].[Cl-].[NH4+].CN(C)[CH2:21][CH2:22]N(C)C>N1C=CC=CC=1>[CH3:13][CH:12]([CH2:11][CH2:10][CH2:9][CH:21]([CH3:22])[CH2:7][CH2:6][CH2:5][C:2]([CH3:1])([OH:16])[C:3]#[C:4][C:4]#[C:3][C:2]([CH3:1])([OH:16])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH3:14]

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 1026523,7,11-Trimethyldodecyn-3-ol

Product 1

HCID 214273422,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diolYield 81.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 1-l. three-necked and round-bottomed flask were placed 10.5 g of 3,7,11-trimethyldodeca-l-yne-3ol, 5.0 g of ammonium chloride, 12.0 g of tetramethylethylenediamine and 675 ml of pyridine. The mixture was reacted at temperatures of 50° - 55°C for 6 hours under an oxygen atmosphere. After completion of the reaction, the alcohol as a starting material was not detected. After distillation of pyridine from the reaction mixture, 300 ml of benzene and 200 ml of water were added to the residue and after decantation, the organic layer was washed with 3N--H2SO4 and then water and dried. The benzene solution was distilled off to give 8.55 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol as viscous liquid. This compound was treated with active carbon and purified in the same manner as in reference 1.

Workup

  1. customthree-necked and round-bottomed flask were placed
  2. customThe mixture was reacted at temperatures of 50° - 55°C for 6 hours under an oxygen atmosphere
  3. customAfter completion of the reaction
  4. distillationAfter distillation of pyridine from the reaction mixture, 300 ml of benzene and 200 ml of water
  5. additionwere added to the residue
  6. washafter decantation, the organic layer was washed with 3N
  7. dry with materialH2SO4 and then water and dried
  8. distillationThe benzene solution was distilled off

Sources & evidence

ORD record
ord-f0cf9cc54fe040e2a95ccff759173245
Source dataset
uspto-grants-1977_03
Patent number
US04011277

Reaction notes

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