1-Chloro-4-nitrobenzene → 2-(4-Methylphenyl)-2-[4-(4-nitrophenoxy)phenyl]hexafluoropropane

HRID 1195446Notes

Reaction equation

HRID 1195446 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.CC(N(C)C)=O.[OH-].[Na+].Cl[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.O>[CH3:23][C:20]1[CH:19]=[CH:18][C:17]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[CH:3][CH:4]=2)([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 148323252-(4-Hydroxyphenyl)-2-(4-methylphenyl)hexafluoropropane

Product 1

HCID 148323272-(4-Methylphenyl)-2-[4-(4-nitrophenoxy)phenyl]hexafluoropropane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

334 g (1 mol) of 2-(4-hydroxyphenyl)-2-(4-methylphenyl)hexafluoropropane, 1.2 dm3 of dimethylacetamide, 200 cm3 of toluene and 44 g of sodium hydroxide were refluxed until it was no longer possible to separate off any water of reaction using a water separator. The toluene was then removed by distillation, 164.4 g (1.1 mol) of 4-chloronitrobenzene were added, and the mixture was refluxed for 48 hours. After the mixture had been cooled to about 0° C., the solid was filtered off, washed with about 100 cm3 of dimethylacetamide and discarded. As much of the dimethylacetamide as possible was removed from the filtrate by vacuum distillation. The oily residue was taken up in 800 cm3 of methanol, a yellow solid precipitating out. The solid was separated off and dried. After the mother liquor had been worked up, a total of 325 g (71% of theory) of a yellow solid were obtained.

Workup

  1. customto separate off
  2. customany water of reaction
  3. additionwere added
  4. temperaturethe mixture was refluxed for 48 hours
  5. filtrationthe solid was filtered off
  6. washwashed with about 100 cm3 of dimethylacetamide
  7. customAs much of the dimethylacetamide as possible was removed from the filtrate by vacuum distillation
  8. customa yellow solid precipitating out
  9. customThe solid was separated off
  10. customdried
  11. customa total of 325 g (71% of theory) of a yellow solid were obtained

Sources & evidence

ORD record
ord-4f902b2b5f8b4d4ba89397844ecb8bf2
Source dataset
uspto-grants-1992_05
Patent number
US05110983

Reaction notes

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