Synthesis of 2,2-diphenylethanol

Preparation of 2,2-diphenylethanol

Preparation of 2,2-diphenylethanol

Preparation of 2,2-diphenylethanol

1,1-Diphenylethylene is added slowly, with stirring, to a solution of sodium borohydride and aluminum chloride in diethylene glycol dimethyl ether (diglyme). The mixture is kept under nitrogen for 3 h at room temperature, then warmed for 1 h on a water-bath. About half of the solvent is distilled off in a vacuum below 40°, and the remainder is washed out with dilute hydrochloric acid and water. The residue is treated with ethanolic sodium hydroxide, and a 20% excess of 30% hydrogen peroxide is dropped in at such a rate that the mixture just boils under reflux. The organic material is taken up in ether and worked up by distillation, affording 87% (86.4 g) of 2,2-diphenylethanol, b.p. 192-194°/20 mm.

J. Amer. Chem. Soc, 78, 5694 (1956).

IUPAC Name

2,2-diphenylethanol

InChI

InChI=1S/C14H14O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11H2

InChI Key

NYLOEXLAXYHOHH-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(CO)C2=CC=CC=C2

Depositor-Supplied Synonyms

2,2-Diphenylethanol, 1883-32-5, beta-Phenylphenethyl alcohol, 2,2-DIPHENYL ETHANOL, 2,2-Diphenyl-ethanol, Benzeneethanol, .beta.-phenyl-, NYLOEXLAXYHOHH-UHFFFAOYSA-N, ST51038040, ACMC-20aojg, AC1Q7BJJ, 2,2-diphenyl-1-ethanol, 2,2-diphenylethan-1-ol, Benzeneethanol, b-phenyl-, AC1L2ME6, AC1Q7BJ5, KSC539O6L, (2,2-Diphenyl)ethyl alcohol, SCHEMBL193835, 196568_ALDRICH, CTK4D9765, NYLOEXLAXYHOHH-UHFFFAOYSA-, DTXSID40172179, NSC4574, NSC 4574, NSC-4574, ZINC1679976, EINECS 217-543-6, AR-1D1645, MFCD00004729, ZINC01679976, AKOS009156878, MCULE-7914963892, RP25616, TRA0074874, AK306994, CJ-06253, CJ-27531, KB-16438, OR013250, OR188884, OR235648, DB-027903, TR-008722, FT-0676589, Y-8843, I14-11815, InChI=1/C14H14O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11H2

Removed Synonyms

MolPort-000-861-065, CID74662, 10298-80-3, 19188-81-9

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