1-Octanol → HCID 178443874, compound

HRID 1441913Notes

Reaction equation

HRID 1441913 reaction equation
[S:1]([O:7][CH2:8][CH3:9])([O:4][CH2:5]C)(=[O:3])=[O:2].C[C:11]1[NH:12][CH:13]=[CH:14][N:15]=1.[CH2:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(O)C>[CH2:8]([O:7][S:1]([O-:4])(=[O:2])=[O:3])[CH2:9][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH2:13]([N+:12]1[CH:23]=[CH:22][N:15]([CH3:14])[CH:11]=1)[CH3:5]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6163Diethyl SulfateHCID 127492-Methylimidazole

Product 1

HCID 178443874HCID 178443874, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 250 ml Schlenk flask, 58.75 g (0.381 moles) of diethyl sulfate was slowly added dropwise to 31.28 g (0.381 moles) of methylimidazole with ice cooling and under a blanket gas. Stirring of the mixture was continued at room temperature over night. After the addition of 62.72 g (0.482 moles; 1.26 equ.) of 1-octanol and 0.67 g of Lewatite K-2629 washed with acetone and dried under high vacuum (acidic ion-exchanger), the mixture was allowed to react over night at 140° C., and at the same time, the by-product ethanol formed was removed from the reaction mixture by sparging with an argon stream. The remaining volatile fractions were subsequently removed under high vacuum at 80° C. The product, 1-ethyl-3-methylimidazolium 1-octyl sulfate, was obtained as a medium-viscous, slightly yellow liquid in quantitative yield.

Workup

  1. waitwas continued at room temperature over night
  2. washwashed with acetone
  3. customdried under high vacuum (acidic ion-exchanger)
  4. customto react over night at 140° C.
  5. customwas removed from the reaction mixture
  6. customby sparging with an argon stream
  7. customThe remaining volatile fractions were subsequently removed under high vacuum at 80° C

Sources & evidence

ORD record
ord-8754e54cf081402da3a660cc3b2305bb
Source dataset
uspto-grants-2010_02
Patent number
US07655803B2

Reaction notes

Loading…