Synthesis of benzyl phenyl sulfide

Preparation of benzyl phenyl sulfide

Thiophenol (57 g., 0.52 mole) is added slowly with stirring to a previously prepared solution of 12 g. (0.52 g. atom) of sodium in 300 ml. of absolute ethanol. Then 68.8 g. (0.54 mole) of benzyl chloride is added dropwise over a period of 1.5 hours, and the mixture is refluxed for 2 hours after completion of the addition. Most of the ethanol is distilled off and the residue while still hot is poured onto 400 g. of ice. The precipitated solid is removed by filtration and washed with two 50-ml. portions of water. It weighs 61 g. (60%) and melts at 40-41°.

Reference: J. Am. Chem. Soc, 52, 2066 (1930).

IUPAC Name

benzylsulfanylbenzene

InChI

InChI=1S/C13H12S/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-10H,11H2

InChI Key

LKMCJXXOBRCATQ-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CSC2=CC=CC=C2

Depositor-Supplied Synonyms

BENZYL PHENYL SULFIDE, 831-91-4, Benzyl(phenyl)sulfane, benzylsulfanylbenzene, Phenyl benzyl sulfide, Benzylphenylsulfide, Benzyl phenyl sulphide, Sulfide, benzyl phenyl, Benzene, [(phenylmethyl)thio]-, Benzylthiobenzene, (benzylsulfanyl)benzene, (phenylmethylthio)benzene, 1,2-Diphenyl-1-thiaethane, LKMCJXXOBRCATQ-UHFFFAOYSA-N, AK116684, ST50406348, benzylphenyl sulfide, (Benzylthio)benzene, benzylphenylthioether, EINECS 212-612-7, NSC 56472, PubChem13528, ACMC-209pri, (phenylmethylsulfanyl)benzene, B29202_ALDRICH, SCHEMBL332623, AC1L21D3, Sulfide, benzyl phenyl (8CI), LKMCJXXOBRCATQ-UHFFFAOYSA-, DTXSID50232172, MolPort-000-151-450, [(Phenylsulfanyl)methyl]benzene #, NSC56472, ZINC1687431, ANW-37660, FCH931042, MFCD00003066, NSC-56472, STL289235, ZINC01687431, AKOS005207312, GS-3129, MCULE-8425906634, RP25799, RTR-025921, TRA0026320, VZ31363, Benzene, ((phenylmethyl)thio)- (9CI), AJ-29900, AN-47757, CC-24493, CJ-27929, I407, KB-47820, OR004040, OR348425, OR348426, SC-46598, AB1004119, AX8116198, DB-056692, TR-025921, B0127, ST24030161, A840523, C-09519, I09-1502, InChI=1/C13H12S/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13/h1-10H,11H2

Removed Synonyms

C13H12S, Benzene, ((phenylmethyl)thio)-, CID13255, C13-H12-S

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