Synthesis of triphenylmethanol

Preparation of triphenylmethanol

To the externally cooled flask containing 0.15 mol of phenylmagnesium bromide a solution of 10 g (or 9.2 ml) of methyl benzoate (or 11 g (10.5 ml) of ethyl benzoate) in 30 ml of absolute ether is placed in the separatory funnel and added dropwise slowly with constant shaking. After all methyl benzoate is added and the reaction subsides, then the funnel is exchanged for the calcium chloride tube and the mixture is refluxed for one-half hour. When the reaction is complete the solution is poured onto a mixture of 100 ml of 10% sulfuric acid and about 50 g of ice contained in a large beaker. The mixture is well stirred so that the intermediate derivative is completely hydrolyzed. The  obtained triphenylmethanol is extracted with ether, the extracted solution is separated from the aqueous solution by means of a separatory funnel. In order to remove magnesium salts completely, the ethereal solution is washed with 10% sulfuric acid and then with water. The ethereal solution is removed by evaporation and crude triphenylmethanol is distilled with steam. The distillation process is discontinued as soon as there is no appreciable amount of water-insoluble material in the distillate. With the removal of the remaining traces of ether and of the impurities, the triphenylmethanol separates as a solid. At the end of the process, the mixture is cooled and the triphenylmethanol is collected by filtration, partially dried, and crystallized from alcohol. The pure triphenylmethanol is colorless, which melts at 162° C. The yield is about 10 g.

Experiments in Organic Chemistry, L. F. Fieser, 69-71, 1941

Preparation of triphenylmethanol

Preparation of triphenylmethanol

Triphenylchloromethane is heated for 10 min in aqueous solution under reflux. After cooling, the triphenylmethanol (triphenyl carbinol) is filtered off and is crystallized from carbon tetrachloride or alcohol from. Yield: 95%, m.p. 162°C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 203, (1973)

IUPAC Name

triphenylmethanol

InChI

InChI=1S/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H

InChI Key

LZTRCELOJRDYMQ-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

TRIPHENYLMETHANOL, Trityl alcohol, 76-84-6, Triphenylcarbinol, Tritanol, Triphenylmethyl alcohol, Methanol, triphenyl-, triphenyl carbinol, Triphenyl methanol, Triphenyl-methanol, diphenyl-phenyl carbinol, Benzenemethanol, .alpha.,.alpha.-diphenyl-, LZTRCELOJRDYMQ-UHFFFAOYSA-N, NSC 4050, triphenylmethan-1-ol, AR-360/42760202, tritylalcohol, tri(phenyl)methanol, PubChem16669, ACMC-1BLZG, AC1L1MKO, SCHEMBL700, UNII-U97Q0OU9KB, AC1Q76QN, Monohydroxyl Triphenylmethane, U97Q0OU9KB, KSC378Q4T, Methanol, triphenyl- (8CI), 134848_ALDRICH, AMBZ0207, CHEMBL118166, 93060_FLUKA, CTK2H8849, LZTRCELOJRDYMQ-UHFFFAOYSA-, Triphenylcarbinol; Trityl alcohol, NSC4050, MolPort-001-780-282, NSC-4050, EINECS 200-988-5, ANW-36898, SBB057388, STK370823, ZINC51498203, AKOS002265728, Benzenemethanol, alpha,alpha-diphenyl-, .alpha.,.alpha.-Diphenyl-benzylalcohol, AM85903, MCULE-5562347436, RP29280, RTR-024592, Triphenylmethyl-containing compound, 13, AK116973, AN-23904, BP-12571, CJ-20675, KB-62138, AB1002216, AI3-08929, AJ-111669, DB-056145, TL8005272, TR-024592, FT-0631329, ST24031966, ST50754320, U-45483, 3B3-036594, F1908-0150, 131612-90-3, InChI=1/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H

Removed Synonyms

Tritol, CID6457, Benzenemethanol,.alpha.-diphenyl-, T0516

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