Hydrochloric Acid → HCID 13199339, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chlorophenol (15.0 g, 0.12 moles) and cyclohexane (8 ml) was distilled to remove cyclohexane and water. To the dry p-chlorophenol was added 3.3 g of zirconium n-propoxide in n-propanol consisting of 21.6% zirconium (0.008 mole) and 10.8% free propanol. The mixture was distilled at atmospheric pressure under nitrogen removing 1.0 g of n-propanol. To the resultant mixture was added methyl disulfide (7.1 g, 0.075 moles). The mixture was heated under nitrogen at reflux for 43 hours during which the temperature increased to 180° C. The mixture was cooled, hydrolyzed by addition of water, treated with concentrated HCl to dissolve solids, and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered, and concentrated on a rotary flash evaporator. GC analysis of the concentrate indicated only two major components, 5.9 g of 4-chlorophenol and 8.1 g of 2-methylthio-4-chlorophenol (62% yield).

Provenance & Evidence