Phenol → HCID 85790137, compound

HRID 597668Notes

Reaction equation

HRID 597668 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH3:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:10]=1.C1(O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][N:16]=[C:17]([Cl:2])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24819Phosphorus pentachlorideHCID 53941281HCID 53941281, compound

Product 1

HCID 85790137HCID 85790137, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture consisting of 7.9 g. (0.038 mole) phosphorus pentachloride, 100 ml. carbon tetrachloride, and 9.05 g. (0.035 mole) benzoic acid 2-[p-(methylthio)phenyl]hydrazide (prepared in Part A above) was heated at the reflux temperature until evolution of gas ceased. The reaction mixture was chilled in ice, and a suspension of 11.3 g. (0.12 mole) phenol in 50 ml. carbon tetrachloride was added. After removing the carbon tetrachloride by evaporation under reduced pressure, the resulting triphenylphosphate solution of the desired product was poured through a column of silica gel. The column was eluted with a mixture of 1 part benzene and 1 part Skellysolve B. After removing the solvents from the eluate by evaporation under reduced pressure, the residue was recrystallized two times from cyclohexane to give benzoyl chloride [p-(methylthio)phenyl]hydrazone having a melting point at 94° to 95° C.

Workup

  1. temperaturewas heated at the reflux temperature until evolution of gas
  2. temperatureThe reaction mixture was chilled in ice
  3. additiona suspension of 11.3 g
  4. customAfter removing the carbon tetrachloride
  5. customby evaporation under reduced pressure
  6. additionthe resulting triphenylphosphate solution of the desired product was poured through a column of silica gel
  7. washThe column was eluted with a mixture of 1 part benzene and 1 part Skellysolve B
  8. customAfter removing the solvents from the
  9. customeluate by evaporation under reduced pressure
  10. customthe residue was recrystallized two times from cyclohexane

Sources & evidence

ORD record
ord-b66d6afb1ff0457cb3ece8dedc0be987
Source dataset
uspto-grants-1977_03
Patent number
US04014932

Reaction notes

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