Synthesis of benzilic acid

Preparation of benzilic acid

Alternative Names: Benzylic acid; Diphenylglycolic acid; 2-Hydroxy-2,2-diphenylacetic acid; Hydroxy(diphenyl)acetic acid;

Preparation of benzilic acid

Preparation of benzilic acid

In a silver or copper crucible 40 g solid potassium hydroxide are melted with a little water, then the liquid is allowed to cool to 150° C, and 10 g dry benzil are added with constant stirring. The benzil melts, and is soon converted into a solid mass of potassium benzilate. As soon as all the oil has disappeared, the whole is dissolved in water and the benzilic acid precipitated by acidifying with hydrochloric acid. When the solution is cold the crystalline matter is filtered off and washed with cold water. The raw acid thus obtained generally contains small quantities of benzoic acid. To remove benzoic acid, the product is boiled in a dish with water until the smell of benzoic acid has disappeared. The benzilic acid, which is not volatile, is then purified by recrystallization from hot water. Yield almost quantitative. Melting point 150° C.

Introduction to the preparation of organic compounds, E. Fisher, 64-65, 1909

IUPAC Name

2-hydroxy-2,2-diphenylacetic acid

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)

InChI Key

UKXSKSHDVLQNKG-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C(=O)O)O

MeSH Synonyms

2,2-diphenyl-2-hydroxyethanoic acid, 2-hydroxy-2,2-diphenylacetic acid, DPHEAc

Depositor-Supplied Synonyms

BENZILIC ACID, Benzylic acid, Diphenylglycolic acid, 76-93-7, 2-Hydroxy-2,2-diphenylacetic acid, hydroxy(diphenyl)acetic acid, Diphenylhydroxyacetic acid, Hydroxydiphenylacetic acid, Glycolic acid, diphenyl-, 2,2-Diphenyl-2-hydroxyacetic acid, Acide diphenylhydroxyacetique, hydroxy(diphenyl)essigs, NSC 2830, alpha-Hydroxy-2,2-diphenylacetic acid, UNII-8F6J993XXR, Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-, Mandelic acid, alpha-phenyl-, alpha-Hydroxy-alpha-phenylbenzeneacetic acid, Mandelic acid, .alpha.-phenyl-, CHEBI:39414, 2,2-Diphenyl-2-hydroxy acetate, Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, UKXSKSHDVLQNKG-UHFFFAOYSA-N, EINECS 200-993-2, 2-hydroxy-2,2-diphenyl-acetic acid, Acide diphenylhydroxyacetique [French], .alpha.,.alpha.-Diphenylglycolic acid, BRN 0521402, .alpha.-Hydroxy-2,2-diphenylacetic acid, AI3-06300, .alpha.,.alpha.-Diphenyl-.alpha.-hydroxyacetic acid, Benzilsaeure, 4hnc, Diphenyl glycolic acid, alpha-phenylmandelic acid, Hydroxydiphenyl acetic acid, AC1L1ML3, AC1Q5SN4, AC1Q71SQ, mandelic acid, |A-phenyl-, SCHEMBL7066, B5194_ALDRICH, Oprea1_231381, KSC489M8N, 8F6J993XXR, CHEMBL578171, 12190_FLUKA, alpha,alpha-Diphenylglycolic acid, BDBM81768, CTK3I9686, HSDB 7709, NSC2830, .alpha.-Hydroxydiphenylacetic acid, BB_SC-0097, NSC-2830, 2,2-Diphenyl 2-hydroxyethanoic acid, AR-1J2132, BBL013081, ICCB1_000122, SBB003299, STK315343, 2-hydroxy-2,2-di(phenyl)acetic acid, AKOS000120948, MCULE-4278216166, RP27748, RTR-016834, NSC_5311391, NCGC00165988-01, AC-13764, AJ-56467, AK112794, AN-23905, KB-75277, LS-32450, OR025277, OR339498, SC-45451, CAS_6581-06-2, alpha,alpha-Diphenyl-alpha-hydroxyacetic acid, B0052, FT-0622673, H2934, ST45138014, .alpha.-Hydroxy-.alpha.-phenylbenzeneacetic acid, S14-0975, T5894502, DIPHENYL-HYDROXY-ACETIC ACID (BENZILIC ACID), 3B3-033148, 0UT, 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

Removed Synonyms

|A,|A-Diphenylglycolic acid, QUINUCLIDINYL BENZILATE, |A-Hydroxydiphenyl acetic acid, CID6463, |A,|A-Diphenyl-|A-hydroxyacetic acid, 4-10-00-01256 (Beilstein Handbook Reference), 25563-02-4, 81276-20-2

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