Phenol → o-(Methylthio)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of phenol (402 grams, 4.2 moles) and toluene (60 ml) was distilled to remove all toluene thereby yielding substantially anhydrous phenol. To the phenol, aluminum turnings (7.5 grams, 0.28 moles) were slowly added at 125° to 140° C. After cessation of hydrogen evolution, methyldisulfide (250 ml, 2.8 moles) was added and the resulting mixture was refluxed overnight at about 170° C. The mixture was then further heated at 170° to 185° C. for 3 hours. All volatile materials were then removed by vacuum evacuation at 20 mm Hg at 170° C. The unreacted phenol was removed by distillation through a 16"×1/2" heated column packed with glass helices. The residue, containing predominately the product ortho-(methylthio)-phenol, was distilled through a 7 cm Vigreax Column yielding 158 grams of the product (b.p. 115°-117° C. at 35 mm psig; 40.0 percent yield).

Provenance & Evidence