Isopropanol → HCID 86612591, compound

HRID 2113394Notes

Reaction equation

HRID 2113394 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, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture that contains 1 g (0.77.10−2 mol) of N,N,3,3-tetramethylbutylamine (Aldrich) and 1.917 g (1.16.10−2 mol) of 1-bromo-3,3-dimethylbutane (Prolabo) and about 4 ml of isopropanol is prepared. 1.23 g (1.16.10−2 mol) of sodium carbonate is then added. This suspension is brought to reflux for 2 days at the temperature of 100° C. A white solid appears, and after this period, about 5 ml of diethyl ether is added to the reaction mixture so as to increase the amount of precipitate. The isopropanol and the diethyl ether are then evaporated at 30° C. by means of a rotary evaporator. The organic product that is formed is extracted from the reaction mixture by means of dichloromethane. Three successive extractions with 10 ml of dichloromethane are carried out. The organic phase that is obtained is evaporated by means of a rotary evaporator. The white solid that is formed is washed with dry diethyl ether and filtered on a nylon membrane (Ø=0.2 μm). 0.8 g (0.27.10−2 mol) of N,N-dimethyl-N,N-di(3,3-dimethylbutyl)ammonium bromide (DMDMBA-Br) is then obtained. The nature of the radical that is obtained was verified by nuclear magnetic resonance of the proton; the results of this analysis are provided below. NMR 1H (D2O, 400 MHz, 25° C., δ ppm /TMS): 0.83 (s, 18H), 1.51-1.55 (m, 4H), 2.91 (s, 6H), 3.18-3.23 (m, 4H).

Workup

  1. customis prepared
  2. waitA white solid appears, and after this period
  3. temperatureto increase the amount of precipitate
  4. customThe isopropanol and the diethyl ether are then evaporated at 30° C. by means of a rotary evaporator
  5. customThe organic product that is formed
  6. extractionis extracted from the reaction mixture by means of dichloromethane
  7. extractionThree successive extractions with 10 ml of dichloromethane
  8. customThe organic phase that is obtained
  9. customis evaporated by means of a rotary evaporator
  10. customThe white solid that is formed
  11. washis washed with dry diethyl ether
  12. filtrationfiltered on a nylon membrane (Ø=0.2 μm)

Sources & evidence

ORD record
ord-0edb0c78dcbe479b8f353ae191b52275
Source dataset
uspto-grants-2008_10
Patent number
US07431913B2

Reaction notes

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