Butyl Chloride → HCID 178448197, compound

HRID 1885502Notes

Reaction equation

HRID 1885502 reaction equation
[Mg:1].[CH2:2](Cl)[CH2:3][CH2:4][CH3:5].[CH2:7]([CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][Na])[CH3:8]>CCCCCCC>[CH2:2]([Mg:1][CH2:10][CH:9]([CH2:7][CH3:8])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8005Butyl ChlorideHCID 5462224MagnesiumHCID 178443583HCID 178443583, compound

Product 1

HCID 178448197HCID 178448197, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To a reaction mixture derived by cooking magnesium metal powder (0.30 g atoms) and n-butyl chloride (0.25 moles) together in 175 ml refluxing heptane was added a solution of 2-ethylhexylsodium (310 ml of 0.65N conc.) in heptane,2 the temperature of reaction not exceeding 42° C. On filtration of the reaction mixture, a solution which was 0.64N in total alkalinity and 0.34M in Mg was obtained. The solution was concentrated to 0.64M (2.2 wt. % Mg) in Mg (Na=0.0025M). Some precipitation of solids occurred in the solution on standing overnight (Mg=0.55M). Sufficient triisobutylaluminum in hexane solution was added to give a final Al concentration corresponding to 3 mole % on the total Mg. All solids immediately dissolved and a very fluid solution resulted. The viscosity of this solution was found to be only 1.25 cps (40° ), a significantly lower value than that listed for a commercial n-butylethylmagnesium in heptane solution at the same magnesium concentration (about 15 cps). Again, the viscosity lowering effect of the 2-ethylhexyl group, as well as its solubilizing properties, was noted. (Di-n-butylmagnesium alone possesses only a very low order [<0.2M] of solubility in hydrocarbon solvents.)

Workup

  1. customthe temperature of reaction not
  2. customexceeding 42° C
  3. filtrationOn filtration of the reaction mixture
  4. customwas obtained
  5. concentrationThe solution was concentrated to 0.64M (2.2 wt. % Mg) in Mg (Na=0.0025M)
  6. customSome precipitation of solids
  7. additionSufficient triisobutylaluminum in hexane solution was added
  8. customto give
  9. concentrationa final Al concentration corresponding to 3 mole % on the total Mg
  10. dissolutionAll solids immediately dissolved
  11. customa very fluid solution resulted
  12. custom1.25 cps (40° )
  13. concentrationa significantly lower value than that listed for a commercial n-butylethylmagnesium in heptane solution at the same magnesium concentration (about 15 cps)

Sources & evidence

ORD record
ord-66bdd3581a8c4c5ebfc0a25c85fcd665
Source dataset
uspto-grants-1992_09
Patent number
US05145600

Reaction notes

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