Synthesis of benzopinacolone (2,2,2-triphenylacetophenone)

Preparation of benzopinacolone

In a round bottom flask, 50 grams of benzopinacol are mixed in 250 ml of glacial acetic acid. The obtained solution is treated with two or three very small crystals of iodine (0.25 grams). The solution is heated to the boiling point under a reflux condenser until the crystals are all dissolved. The red solution is boiled for additional 5-10 minutes. On cooling the benzopinacolone separates as a stiff paste, which is treated with a small amount of alcohol, the crystals of benzopinacolone are collected and wash with alcohol in order to free from iodine. The benzopinacolone is obtained pure, 95% yield and with melting point 179-180° C.

Experiments in Organic Chemistry, L. F. Fieser, 204-205, 1941

IUPAC Name

1,2,2,2-tetraphenylethanone

InChI

InChI=1S/C26H20O/c27-25(21-13-5-1-6-14-21)26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

InChI Key

CFBBKHROQRFCNZ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

Depositor-Supplied Synonyms

2,2,2-Triphenylacetophenone, Tetraphenylethanone, 466-37-5, Benzopinacolone, Phenyl trityl ketone, Ethanone, tetraphenyl-, 1,2,2,2-Tetraphenylethanone, Acetophenone, 2,2,2-triphenyl-, SBB057270, 1,2,2,2-tetraphenylethan-1-one, NSC194, beta-Benzopinacolone, tetraphenylethan-1-one, .beta.-Benzopinacolone, ACMC-1AD2A, AC1L28XB, AC1Q5ET2, 216690_ALDRICH, SCHEMBL1508202, CFBBKHROQRFCNZ-UHFFFAOYSA-, CTK4I9499, 1,2,2,2-tetra(phenyl)ethanone, NSC-194, NSC2820, CFBBKHROQRFCNZ-UHFFFAOYSA-N, Ethanone,1,2,2,2-tetraphenyl-, MolPort-001-779-897, 1,2,2,2-Tetraphenyl-1-ethanone, NSC-2820, EINECS 207-375-1, ANW-30462, AR-1L6551, ZINC03861523, AKOS015904159, AC-13481, AN-45117, AI3-18040, DB-019586, TC-119207, ST50826257, .omega.,.omega.,.omega.-Triphenylacetophenone, I14-1788, 3B3-001635, InChI=1/C26H20O/c27-25(21-13-5-1-6-14-21)26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

Removed Synonyms

CID68049, T1207, 49736-43-8

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