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Benzilic acid



Benzilic acid
IUPAC name Hydroxy(diphenyl)acetic acid
Other names α,α-Diphenyl-α-hydroxyacetic acid, α,α-Diphenylglycolic acid, α-Hydroxydiphenyl acetic acid, 2,2-Diphenyl-2-hydroxyacetic acid, 2-Hydroxy-2,2-diphenylacetic acid, Diphenyl glycolic acid, Hydroxydiphenyl acetic acid, BZ
Identifiers
CAS number 76-93-7
SMILES OC(C(O)=O)(c1ccccc1)c2ccccc2
Properties
Molecular formula C14H12O3
Molar mass 228.25 g/mol
Appearance white solid
Density 1.08 g/cm3
Melting point

150 - 152 °C

Boiling point

180 °C (17.3 hPa)

Solubility in water 2 g/l (20 °C)
Hazards
NFPA 704
1
2
0
 
R-phrases R22
S-phrases S23, S24, S25, S28, S36, S37, S45
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Benzilic acid is a white crystalline aromatic acid soluble in many primary alcohols. It can be prepared by heating mixture of benzil, alcohol and potassium hydroxide. The other preparation way is through benzaldehyde, which dimerizates to benzil and it is further transformed by benzilic acid rearrangement to benzilic acid. This reaction was also the first example of benzilic acid rearrangement preformed by Liebig in 1838.[1]

Additional recommended knowledge

Benzilic acid is used in organic synthesis, as a base point for preparation of glycollate pharmaceuticals and some hallucinogenic drugs.

See also

References

  1. ^ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie 25: 1-31. doi:10.1002/jlac.18380250102.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzilic_acid". A list of authors is available in Wikipedia.
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