Synthesis of benzil

Preparation of benzil

Alternative Names: Diphenylethanedione; Dibenzoyl; Diphenylglyoxal; 1,2-Diphenylethane-1,2-dione;

Preparation of benzil

Preparation of benzil

20 g benzoin are heated with nitric acid (d=1.41 g/ml) on the water-bath. A vigorous reaction takes place: the crystals soon change into a yellow oil, which is at first a mixture of benzil and benzoin. By frequent shaking care is taken that the oil comes into close contact with the nitric acid. The oxidation takes 1-2 hours. The completion of the conversion is best recognised by means of Fehling’s solution. To carry out the test, a drop of the oil is poured into water, where it at once crystallizes; the crystals are dissolved in alcohol and diluted with water; Fehling’s solution is then added and the liquid is warmed to 60-70° C. As long as benzoin is still present, a precipitate of cuprous oxide is formed. As soon as the oxidation is finished the product is poured into water, and when the crystalline mass has set it is dissolved in hot alcohol. On cooling the benzil separates out in splendid yellow prisms. The yield is very good and the benzil melts at 95° C.

Introduction to the preparation of organic compounds, E. Fisher, 62-63, 1909

IUPAC Name

1,2-diphenylethane-1,2-dione

InChI

InChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H

InChI Key

WURBFLDFSFBTLW-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

benzil, diphenyl-alpha-beta-ketone, diphenylethane-1,2-dione, diphenylethanedione

Depositor-Supplied Synonyms

BENZIL, Diphenylethanedione, Dibenzoyl, Diphenylglyoxal, 1,2-Diphenylethane-1,2-dione, 134-81-6, Bibenzoyl, 1,2-Diphenylethanedione, Ethanedione, diphenyl-, Glyoxal, diphenyl-, diphenylethane-1,2-dione, 1,2-ethanedione, 1,2-diphenyl-, Diphenyldiketon, NSC 220315, Diphenyl-alpha,beta-diketone, CCRIS 6179, CHEMBL189886, CHEBI:51507, 1,2-diphenyl-ethane-1,2-dione, Diphenyl-.alpha.,.beta.-diketone, WURBFLDFSFBTLW-UHFFFAOYSA-N, EINECS 205-157-0, 1,2-dione, WY-20910, AI3-00898, WLN: RVVR, AB-131/13435226, diphenyl-alpha-beta-ketone, SCHEMBL66, AC1L1RFD, p-(phenylglyoxalyl)benzene, ACMC-209u2d, B5151_ALDRICH, DSSTox_CID_24380, DSSTox_RID_80184, DSSTox_GSID_44380, Dibenzoyl; Diphenylethanedione, KSC468S8N, B0383_SIGMA, UNII-S85X61172J, 12150_FLUKA, BDBM22722, NSC4041, MolPort-000-657-276, Benzil(Diphenylethane-1,2-Dione), ACN-S002454, C14H10O2, NSC-4041, Tox21_302031, ANW-43235, DNC005443, NSC220315, SBB094341, STL283960, Wy 20910, ZINC01672966, AKOS000120196, MCULE-1752553253, NE10261, NSC-220315, RP26564, RTR-035640, S85X61172J, NCGC00255924-01, AN-23093, CAS-134-81-6, CJ-06154, CJ-27228, LS-32435, OR025253, OR191720, AB1003003, KB-310885, TR-035640, B0050, B0221, FT-0622670, ST50188110, C20226, 1,2-ETHANEDIONE,1,2-DIPHENYL BENZIL, T6435775, I14-13873, 3B3-033051, 16510-35-3, InChI=1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10

Removed Synonyms

CID8651, C006697

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *