Synthesis of benzyl phenyl ether

Preparation of benzyl phenyl ether

Preparation of benzyl phenyl ether

Preparation of benzyl phenyl ether

To prepare the benzyl phenyl ether, 0.25 g gramequivalent of metallic sodium is dissolved in 300 ml of absolute ethanol to which the phenol, dissolved in a little absolute ethanol is then added. After the addition of the 0.2 mole of benzyl chloride (alternatively benzyl bromide or benzyl iodide),  the mixture is heated under reflux with stirring and exclusion of moisture for 5 hours. The alcohol is distilled off from the reaction mixture to a substantial extent through a 20-cm Vigreux column with stirring and the cooled distillation residue is poured into 100 ml of 5% caustic sodium carbonate; the organic phase is extracted several times with diethyl ether, washed with water, and dried with calcium chloride; the solvent is distilled off, and the residue is fractionated or recrystallized from ethanol. Unchanged phenol can be recovered by acidifying the aqueous alkaline solution and extracting it with ether. The yield of benzyl phenyl ether 80%, m.p. 40°C; b.p. 286-287 °C;

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 208-210, (1973)

IUPAC Name

phenoxymethylbenzene

InChI

InChI=1S/C13H12O/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-10H,11H2

InChI Key

BOTNYLSAWDQNEX-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)COC2=CC=CC=C2

Depositor-Supplied Synonyms

Benzyl phenyl ether, (benzyloxy)benzene, 946-80-5, Phenyl benzyl ether, benzyloxy-benzene, Benzene, (phenoxymethyl)-, Ether, benzyl phenyl, BENZYLPHENYLETHER, Benzyloxybenzene, phenoxymethylbenzene, .alpha.-Phenylanisole, Anisole, .alpha.-phenyl-, BOTNYLSAWDQNEX-UHFFFAOYSA-N, NSC 77971, (phenylmethoxy)benzene, ST092323, benzylphenyl ether, alpha-Phenylanisole, phenylmethoxybenzene, (phenoxymethyl)benzene, (Phenoxymethyl)-benzene, Anisole, alpha-phenyl-, AC1L2DWG, Benzene,(phenoxymethyl)-, ACMC-209rt5, NCIOpen2_000787, UNII-BUE863N0L8, SCHEMBL61660, Ether, benzyl phenyl (8CI), ARONIS24218, 404284_ALDRICH, BUE863N0L8, CHEMBL1796019, BDBM86789, Benzyl phenyl ether analogue, 6a, MolPort-000-159-335, Benzene, (phenoxymethyl)- (9CI), NSC77971, ZINC1713876, EINECS 250-571-7, ANW-40311, NSC-77971, SBB008247, STL289438, ZINC01713876, AKOS003630953, MCULE-8592623013, RTR-031122, VZ31362, AC-21019, AJ-30826, AK135803, CJ-29068, OR003082, OR256657, DB-057520, KB-209151, TR-031122, B0433, FT-0622778, A819712, I14-52092, 3B3-007071, InChI=1/C13H12O/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-10H,11H

Removed Synonyms

Phenoxytoluene, CID70352, 28994-41-4, 31324-44-4

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