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The main image on the page incorrectly showed phenylethyl potassium instead of benzyl potassium, I made a new image that shows benzyl potassium and uploaded it.
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Revision as of 07:23, 23 January 2018

Benzyl potassium
Names
Other names
Potassium benzyl
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2;
    Key: OQLLVOGBAKFMIS-UHFFFAOYSA-N
  • InChI=1/C7H7.K/c1-7-5-3-2-4-6-7;/h2-6H,1H2;/rC7H7K/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
    Key: OQLLVOGBAKFMIS-QPGMTJJQAI
  • [K]Cc1ccccc1
Properties
C7H7K
Molar mass 130.23 g/mol
Appearance Orange solid
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Ignites in air
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzyl potassium is an organopotassium compound with the formula C6H5CH2K. It is an orange solid that is so extremely basic that it is compatible only with hydrocarbon solvents.

Synthesis

One early synthesis proceeds by two-step transmetallation reaction via p-tolylpotassium:[1]

(CH3C6H4)2Hg + 2 K → 2 CH3C6H4K + Hg
CH3C6H4K → KCH2C6H5

A modern synthesis involves the reaction of butyllithium, potassium tert-butoxide, and toluene.[2] Although potassium hydride can also be used as a strong base for preparing potassium salts, benzyl potassium has the advantage of being molecular and hence more fast-acting.

References

  1. ^ Gilman, Henry; Pacevitz, Henry A; Baine, Ogden (1940). "Benzylalkali Compounds1". Journal of the American Chemical Society. 62 (6): 1514. doi:10.1021/ja01863a054.
  2. ^ Lochmann, L; Trekoval, J (1987). "Lithium-potassium exchange in alkyllithium/potassium t-pentoxide systems". Journal of Organometallic Chemistry. 326: 1. doi:10.1016/0022-328X(87)80117-1.