Diethyl Sulfate → HCID 23037208, compound

HRID 1709139Notes

Reaction equation

HRID 1709139 reaction equation
[CH:1]1([CH:13]([CH3:16])[CH2:14][OH:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].S(OCC)(O[CH2:23][CH3:24])(=O)=O>O1CCCC1>[CH2:23]([O:15][CH2:14][CH:13]([CH:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16])[CH3:24]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 98159802-Cyclododecylpropan-1-ol

Product 1

HCID 23037208HCID 23037208, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 g of 2-cyclododecylpropan-l-ol were stirred with 4 g of sodium hydride in 150 ml of tetrahydrofuran for two hours at the boiling temperature excluding air. 6 g of diethyl sulfate were then added dropwise, and the mixture was refluxed for a further two hours. The cooled reaction mixture was poured onto ice and extracted by stirring with 20 ml of 10% strength NaOH and 50 ml of tert.-butyl methyl ether. The aqueous layer was again extracted by shaking with tert.-butyl methyl ether, and the combined organic layers were again extracted by shaking with 10% strength NaOH and distilled. After removal of the solvents, 9.5 g of 2-cyclododecylpropyl ethyl ether were obtained at 92-95° C. and 0.2 mbar.

Workup

  1. temperaturethe mixture was refluxed for a further two hours
  2. customThe cooled reaction mixture
  3. additionwas poured onto ice
  4. extractionextracted
  5. extractionThe aqueous layer was again extracted
  6. stirringby shaking with tert.-butyl methyl ether
  7. extractionthe combined organic layers were again extracted
  8. stirringby shaking with 10% strength NaOH
  9. distillationdistilled
  10. customAfter removal of the solvents

Sources & evidence

ORD record
ord-99c949a92df0472da48a109fc0d45511
Source dataset
uspto-grants-1990_08
Patent number
US04948780

Reaction notes

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