Acetic Acid → (4-Aminophenyl)[4-(propan-2-yl)phenyl]methanone

HRID 1648826Notes

Reaction equation

HRID 1648826 reaction equation
O.C(O)(=O)C.[CH:6]([C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)([CH3:8])[CH3:7].C(=O)([O-])[O-].[Na+].[Na+]>[Fe].C(O)C>[CH:6]([C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 18956697HCID 18956697, compound

Product 1

HCID 170293(4-Aminophenyl)[4-(propan-2-yl)phenyl]methanone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
95 °C

Procedure

800 parts of water, 250 parts of iron chips and 28 parts of acetic acid are initially introduced, and the mixture is heated to 95° C. and stirred for 1 hour at 95° C. It is then cooled to 90° C., 800 parts of ethanol are added, and 55 parts of 4-isopropyl-4'-nitrobenzophenone are added in a solid form in small portions in the course of 30 minutes. The mixture is heated for 8 hours under reflux, its pH is adjusted to 9 by means of 44 parts of sodium carbonate solution, 600 parts of ethanol are added, heating under reflux is carried out for 15 hours, the mixture is filtered hot and the residue is washed three times with 200 parts each of hot ethanol. Ethanol is distilled off from the combined filtrates and the aqueous bottom is cooled down. The precipitated crystals are then filtered off and dried in vacuo. 45.5 parts of 4-isopropyl- 4'-aminobenzophenone having a melting point of 110° C. are obtained. The valuable dyestuff of the formula VI ##STR7## can be prepared from 4-isopropyl-4'-aminobenzophenone as indicated in German Offenlegungsschrift No. 2,001,821, Table 1, Example 15.

Workup

  1. temperatureIt is then cooled to 90° C.
  2. temperatureThe mixture is heated for 8 hours
  3. temperatureunder reflux
  4. additionare added
  5. temperatureheating
  6. temperatureunder reflux
  7. waitis carried out for 15 hours
  8. filtrationthe mixture is filtered hot
  9. washthe residue is washed three times with 200 parts each of hot ethanol
  10. distillationEthanol is distilled off from the combined filtrates
  11. temperaturethe aqueous bottom is cooled down
  12. filtrationThe precipitated crystals are then filtered off
  13. customdried in vacuo

Sources & evidence

ORD record
ord-8709ff01a2d64923b4a9de3433598c1a
Source dataset
uspto-grants-1983_11
Patent number
US04413144

Reaction notes

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