Isopropanol → HCID 86612591, compound

HRID 1442462Notes

Reaction equation

HRID 1442462 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:3].[Br:10][CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14].C(O)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[Br-:10].[CH3:1][N+:2]([CH3:3])([CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 1371371-Bromo-3,3-dimethylbutaneHCID 19033341HCID 19033341, compound

Product 1

HCID 86612591HCID 86612591, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture was prepared containing 1 g (0.77×10−2 moles) of N,N,3,3-tetramethylbutylamine (Aldrich) and 1.917 g (1.16×10−2 moles) of 1-bromo-3,3-dimethylbutane (Prolabo) and about 4 ml of isopropanol. Next, 1.23 g (1.16×10−2 mole) of sodium carbonate was added. This suspension was heated under reflux for 2 days at a temperature of 100° C. A white solid appeared and after this time, about 5 ml of diethylether was added to the reaction mixture to increase the quantity of precipitate. The isopropanol and diethylether were then evaporated off at 30° C. using a rotary evaporator. The organic product formed was extracted from the reaction mixture using dichloromethane. Three successive extractions with 10 ml of dichloromethane were carried out. The organic phase obtained was evaporated using a rotary evaporator. The white solid formed was washed with dry diethylether and filtered over a nylon membrane (diameter=0.2 μm). 0.8 g (0.27×10−2 moles) of N,N-dimethyl-N,N-di(3,3-dimethylbutyl)ammonium bromide (DMDMBA-Br) was obtained. The nature of the species obtained was verified by proton nuclear magnetic resonance; the results of this analysis are given below:

Workup

  1. customA mixture was prepared
  2. temperatureThis suspension was heated
  3. temperatureto increase the quantity of precipitate
  4. customThe isopropanol and diethylether were then evaporated off at 30° C.
  5. customa rotary evaporator
  6. customThe organic product formed
  7. extractionwas extracted from the reaction mixture
  8. extractionThree successive extractions with 10 ml of dichloromethane
  9. customThe organic phase obtained
  10. customwas evaporated
  11. customa rotary evaporator
  12. customThe white solid formed
  13. washwas washed with dry diethylether
  14. filtrationfiltered over a nylon membrane (diameter=0.2 μm)

Sources & evidence

ORD record
ord-2f87da3be48a451ab93176578c9d3f3e
Source dataset
uspto-grants-2010_02
Patent number
US07658909B2

Reaction notes

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