Phenol → HCID 73796067, compound

HRID 1581125Notes

Reaction equation

HRID 1581125 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][NH:10][C:11](=O)[C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21].C1(O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][N:10]=[C:11]([Cl:21])[C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

5

Reactant 3

HCID 996Phenol2×HCID 24819Phosphorus pentachlorideHCID 21561699HCID 21561699, compound

Product 1

HCID 73796067HCID 73796067, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
20 °C

Procedure

A suspension of 1-(4,5-dichloro-2-nitrophenyl)-2-trimethylacetyl-hydrazine (739 g.) and phosphorus pentachloride (517 g.) in carbon tetrachloride (4.8 liters) is heated until the evolution of gas ceases, the reaction mixture being taken progressively to the reflux temperature. To the solution obtained there is added, after cooling to 20°C., a solution of phenol in carbon tetrachloride (3.36 liters) containing 2.36 moles of phenol per liter. The reaction mixture is then heated at the reflux temperature until the evolution of gas finishes. It is then cooled to 20°C., filtered and the resulting solution is concentrated under reduced pressure (20 mm. Hg.) at 60°C. The residue is purified by chromatography on "Kieselgel", elution being effected with a mixture of heptane and diethyl ether (9.5 - 0.5 by volume). After recrystallisation from isopropanol and then heptane, there is obtained 1-(4,5-dichloro-2-nitrophenyl-hydrazono)-1-chloro-2,2-dimethylpropane (498 g.) melting at 99° - 100°C.

Workup

  1. temperatureis heated until the evolution of gas ceases
  2. customTo the solution obtained there
  3. additionis added
  4. temperatureThe reaction mixture is then heated at the reflux temperature until the evolution of gas finishes
  5. temperatureIt is then cooled to 20°C.
  6. filtrationfiltered
  7. concentrationthe resulting solution is concentrated under reduced pressure (20 mm. Hg.) at 60°C
  8. customThe residue is purified by chromatography on "Kieselgel", elution
  9. additionbeing effected with a mixture of heptane and diethyl ether (9.5 - 0.5 by volume)
  10. customAfter recrystallisation from isopropanol

Sources & evidence

ORD record
ord-c6dd794c64074b3cb8c387f25b4e0989
Source dataset
uspto-grants-1976_01
Patent number
US03935315

Reaction notes

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