:Benzilic acid
{{distinguish|benzyl alcohol}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443415569
| ImageFile = Benzilsäure.svg
| ImageSize = 180
| ImageAlt = Skeletal formula of benzilic acid
| ImageFile1 = Benzilic-acid-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the benzilic acid molecule
| PIN= Hydroxydi(phenyl)acetic acid{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 748 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}
| OtherNames = 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
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6220
| 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)
| InChIKey = UKXSKSHDVLQNKG-UHFFFAOYAV
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 578171
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UKXSKSHDVLQNKG-UHFFFAOYSA-N
| CASNo = 76-93-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 6463
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39414
| Gmelin = 281752
| Beilstein = 521402
| EINECS = 200-993-2
| UNII = 8F6J993XXR
| SMILES = O=C(O)C(O)(c1ccccc1)c2ccccc2
}}
|Section2={{Chembox Properties
| C=14 | H=12 | O=3
| Appearance = white solid
| Density = 1.08 g/cm3
| MeltingPtC = 150 to 152
| MeltingPt_notes =
| BoilingPtC = 180
| BoilingPt_notes = (17.3 hPa)
| Solubility = 2 g/L (20 °C)
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302}}
| PPhrases = {{P-phrases|264|270|301+312|330|501}}
}}
}}
Benzilic acid is an organic compound with formula {{chem|C|14|H|12|O|3}} or ({{chem|C|6|H|5}})2(HO)C(COOH). It is a white crystalline aromatic acid, soluble in many primary alcohols.
Preparation
Benzilic acid can be prepared by heating a mixture of benzil, ethanol, and potassium hydroxide.
Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction.{{cite journal | author = Liebig, J.|title=Ueber Laurent's Theorie der organischen Verbindungen|journal = Annalen der Chemie |year = 1838|volume = 25| pages = 1–31|doi=10.1002/jlac.18380250102|author-link=Justus Liebig|url=https://zenodo.org/record/1426927}}
Uses
Benzilic acid is used in the manufacture of glycollate pharmaceuticals including clidinium, dilantin, flutropium, and mepenzolate which are antagonists of the muscarinic acetylcholine receptors.
It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) which is regulated by the Chemical Weapons Convention. It is also monitored by law enforcement agencies of many countries, because of its use in the manufacture in hallucinogenic drugs."[https://web.archive.org/web/20070209234151/http://cbwinfo.com/Chemical/Precursors/p25.html Nerve Agent Precursors: Benzilic acid and Methyl Benzilate]", Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
Benzilic acid can be reduced with hydroiodic acid to give diphenylacetic acid [117-34-0].https://prepchem.com/synthesis-of-diphenylacetic-acid/[https://archive.org/details/Cumming1937/page/n211/mode/2up Systematic organic chemistry, by W. M. Cumming, 192-193, 1937].
References
{{Reflist}}
External links
- [https://web.archive.org/web/20071017042806/http://physchem.ox.ac.uk/MSDS/BE/benzilic_acid.html Safety MSDS data]
- [http://cat.inist.fr/?aModele=afficheN&cpsidt=15377537 Solubility in alcohols]
- [http://www.cerlabs.com/experiments/10875407439.pdf Converting Benzaldehyde to Benzilic Acid]
- [http://www.miracosta.edu/home/dlr/211exp10.htm Synthesis of Benzilic Acid]