Hydrochloric Acid → Tri-n-octylmethylmethane

HRID 2582

Reaction equation

HRID 2582 reaction equation
[CH2:1]([C:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[Ca+2].[Cl-].Cl.[CH2:31](C(Cl)(CCCCCCCC)CCCCCCCC)CCCCCCC.C[Al](C)C>C(Cl)Cl>[CH2:1]([C:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 872399-Octylheptadecan-9-olHCID 5284359Calcium ChlorideHCID 16682925TrimethylaluminumHCID 19690384Tri-n-octylmethylchloride

Product 1

HCID 19690391Tri-n-octylmethylmethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

This compound may be prepared in the following manner. Three moles of 1-bromooctane are slowly added to 3 moles of magnesium turnings in 0.6 liters of anhydrous ethyl ether (nitrogen atmosphere). One mole of diethyl carbonate in 0.151 anhydrous ethyl ether is slowly added to the mixture. The mixture is stirred for one hour at 30° C., then the mixture is slowly poured into 1.8 liters of a cold 10% HCl solution. The organic layer is dried with magnesium sulfate and the ethyl ether is evaporated off to give tri-n-octylcarbinol. One mole of tri-n-octylcarbinol is added to a mixture of 0.2 liters of methylene chloride and 0.32 moles calcium chloride. Approximately 1.5 moles of HCl gas is slowly bubbled through the solution. The product mixture is then washed with 1 liter of a 10% sodium carbonate solution. The organic layer is dried with magnesium sulfate and the methylene chloride is evaporated off. One mole of tri-n-octylmethylchloride is added to 0.75 liters of methylene chloride and the solution is blanketed with nitrogen and is cooled to 0° C. 0.33 moles of trimethylaluminum is then added and the mixture is allowed to warm to room temperature. The mixture is slowly quenched with 50 ml of water followed by washing with 1 liter of a 10% HCl solution. The organic layer is dried with magnesium sulfate and the solvent is evaporated to give tri-n-octylmethylmethane.

Workup

  1. washThe product mixture is then washed with 1 liter of a 10% sodium carbonate solution
  2. dry with materialThe organic layer is dried with magnesium sulfate
  3. customthe methylene chloride is evaporated off
  4. temperatureto warm to room temperature
  5. customThe mixture is slowly quenched with 50 ml of water
  6. washby washing with 1 liter of a 10% HCl solution
  7. dry with materialThe organic layer is dried with magnesium sulfate
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b0a83914dba048c6a657be3218f2bd5a
Source dataset
uspto-grants-1998_03
Patent number
US05728907

Linked notes

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