1-Octanol → HCID 178443872, compound

HRID 1441914Notes

Reaction equation

HRID 1441914 reaction equation
[S:1]([O:6]C)([O:4][CH3:5])(=[O:3])=[O:2].C([C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)CCC.[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:5]([O:4][S:1]([O-:6])(=[O:3])=[O:2])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH2:21]([N+:16]1[CH:15]=[CH:14][N:13]([CH3:5])[CH:12]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 6497Dimethyl SulfateHCID 118153512-butyl-1H-imidazole

Product 1

HCID 178443872HCID 178443872, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 250 ml Schlenk flask, 48.04 g (0.381 moles) of dimethyl sulfate was slowly added dropwise to 47.31 g (0.381 moles) of butylimidazole 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 Dowex ion-exchanger washed with acetone and dried under high vacuum, the mixture was allowed to react over night at 140° C., and at the same time, the by-product methanol 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-butyl-3-methylimidazolium 1-octyl sulfate, was obtained as a viscous, slightly yellow liquid in quantitative yield. The product does not contain any detectable amounts of Cl− contamination (AgNO3 test; <3 ppm).

Workup

  1. waitwas continued at room temperature over night
  2. washwashed with acetone
  3. customdried under high vacuum
  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-218402e4a71a463f810bb19150e54d1a
Source dataset
uspto-grants-2010_02
Patent number
US07655803B2

Reaction notes

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