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
Identifiers
CAS number	76-93-7^Y
ChemSpider	6220^Y
ChEBI	CHEBI:39414^Y
ChEMBL	CHEMBL578171^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(O)(c1ccccc1)c2ccccc2
InChI InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16)^Y Key: UKXSKSHDVLQNKG-UHFFFAOYSA-N^Y InChI=1/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) Key: UKXSKSHDVLQNKG-UHFFFAOYAV
Properties
Molecular formula	C₁₄H₁₂O₃
Molar mass	228.24 g mol⁻¹
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
R-phrases	R22
S-phrases	S23, S24, S25, S28, S36, S37, S45
NFPA 704	1 2 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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 performed by Liebig in 1838.^[1]

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

References

^ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie 25: 1–31. doi:10.1002/jlac.18380250102.