Hydrochloric Acid → HCID 13199339, compound

Temperature

180 °C

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).

1. distillationwas distilled
2. customto remove cyclohexane and water
3. additionTo the dry p-chlorophenol was added 3.3 g of zirconium n-propoxide in n-propanol
4. distillationThe mixture was distilled at atmospheric pressure under nitrogen removing 1.0 g of n-propanol
5. temperatureThe mixture was heated under nitrogen
6. temperatureat reflux for 43 hours during which the temperature
7. temperatureThe mixture was cooled
8. dissolutionto dissolve solids
9. extractionextracted with ether
10. dry with materialThe ether extracts were dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated on a rotary flash evaporator

ORD record

ord-81c74c0a58304e18a954e3173c7768f4

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599451