Phenol → HCID 85443899, compound

HRID 597667Notes

Reaction equation

HRID 597667 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]1([NH:13][NH:14][C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:7]1([NH:13][N:14]=[C:15]([Cl:2])[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24819Phosphorus pentachlorideHCID 53785654HCID 53785654, compound

Product 1

HCID 85443899HCID 85443899, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture consisting of 14.2 g. (0.068 mole) phosphorus pentachloride, 100 ml. carbon tetrachloride, and 16.78 g. (0.065 mole) p-(methylthio)benzoic acid 2-phenylhydrazide (prepared in Part A above) was reacted at 25° C. until evolution of gas ceased. The reaction mixture was then heated to the reflux temperature and a clear solution resulted. The solution was chilled in ice and a suspension of 20.7 g. (0.22 mole) phenol in 50 ml. carbon tetrachloride was added. After removing the carbon tetrachloride by evaporation on a rotary evaporator at 31° C. the resulting suspension of product in triphenylphosphate was filtered. The filter cake was washed with technical hexane (Skellysolve B, a mixture of isomeric hexanes having a boiling range between 146° and 156° Fahrenheit), and then was washed with diethyl ether. Crystallization from 75 ml. ethyl acetate gave 8.10 g. (44.9% yield) of p-(methylthio)benzoyl chloride phenylhydrazone having a melting point of 138.5° to 142.5° C. Recrystallization from a mixture of ethyl acetate and the Skellysolve B gave the compound with the same melting point.

Workup

  1. customwas reacted at 25° C. until evolution of gas
  2. temperatureThe reaction mixture was then heated to the reflux temperature
  3. customa clear solution resulted
  4. temperatureThe solution was chilled in ice
  5. additiona suspension of 20.7 g
  6. customAfter removing the carbon tetrachloride
  7. customby evaporation
  8. customon a rotary evaporator at 31° C.
  9. additionthe resulting suspension of product in triphenylphosphate
  10. filtrationwas filtered
  11. washThe filter cake was washed with technical hexane (Skellysolve B
  12. additiona mixture of isomeric hexanes having a boiling range between 146° and 156° Fahrenheit), and
  13. washthen was washed with diethyl ether
  14. customCrystallization from 75 ml
  15. customethyl acetate gave 8.10 g

Sources & evidence

ORD record
ord-7082f2f0349440e8b7b3bd3656df4745
Source dataset
uspto-grants-1977_03
Patent number
US04014932

Reaction notes

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