Methane → Zinc pivalate

HRID 920861Notes

Reaction equation

HRID 920861 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C[Li].C.[Cl-].[Cl-].[Zn+2:13].C1COCC1>>[C:1]([O-:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Zn+2:13].[C:1]([O-:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 5

HCID 297MethaneHCID 6417Pivalic acidHCID 8028TetrahydrofuranHCID 3007855ZincchlorideHCID 178418348HCID 178418348, compound

Product 1

HCID 19435776Zinc pivalate

Conditions

Temperature
0 °C

Procedure

Pivalic acid (20.4 g, 22.6 mL, 200 mmol) is placed in a dry and argon-flushed 500 mL Schlenk-flask equipped with a magnetic stirring bar and a septum, and the pivalic acid is dissolved in dry THF (100 mL). The solution is cooled to 0° C. and methyllithium (135 mL, 1.63 M in diethyl ether, 220 mmol) is added dropwise. After the evolution of methane gas has stopped, ZnCl2 in THF (100 mL, 1.0 M, 100 mmol) is added and the mixture is stirred for 2 h at 25° C. The solvent is removed in vacuo and zinc pivalate.2LiCl (2a) is obtained as a colourless solid in quantitative yield.

Workup

  1. customa dry
  2. customargon-flushed 500 mL Schlenk-flask
  3. customequipped with a magnetic stirring bar
  4. dissolutiona septum, and the pivalic acid is dissolved in dry THF (100 mL)
  5. customThe solvent is removed in vacuo and zinc pivalate

Sources & evidence

ORD record
ord-f1f5fe2877114a93bc7fe90e20f213f2
Source dataset
uspto-grants-2016_03
Patent number
US09273070B2

Reaction notes

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