Benzilic acid
From Wikipedia, the free encyclopedia
| 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 |
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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.
[edit] See also
[edit] References
- ^ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie 25: 1–31. doi:.
