Methane → HCID 14832341, compound

HRID 1195450Notes

Reaction equation

HRID 1195450 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)=[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.[H][H].O.C>C(OCC)(=O)C.[Pd].Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=3)=[CH:19][CH:18]=2)([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 962WaterHCID 14832340HCID 14832340, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14832341HCID 14832341, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

22.8 g (0.05 mol) of 2-(4-aminophenyl)-2-[4-(3-nitrophenoxy)phenyl]hexafluoropropane were dissolved in 600 cm3 of ethyl acetate, 1 g of palladium on charcoal was added, and the mixture was reduced in a 1 dm3 steel autoclave at about 25° C. using hydrogen (100 bar). When the take-up of hydrogen was complete, the catalyst was filtered off and all the ethyl acetate was removed. The oily, brown crude product was chromatographed over basic alumina using ethyl acetate as eluent. The principal fraction was evaporated to dryness, giving 18 g of a highly viscous, pale yellow residue. 9.5 g of the pale yellow residue were suspended in 100 cm3 of hydrochloric acid (1:1), and 400 cm3 of water were added at the boiling point. The turbid solution was treated twice at the boiling point with 5 g of activated charcoal in each case. The clear, colorless solution was cooled to 20° C., a white solid precipitating out. The suspension was adjusted to a pH of 8-9 under a protective gas (nitrogen) using dilute ammonia solution. The solid was, under a protective gas, filtered off, washed with water and dried.

Workup

  1. filtrationthe catalyst was filtered off
  2. customall the ethyl acetate was removed
  3. customThe oily, brown crude product was chromatographed over basic alumina
  4. customThe principal fraction was evaporated to dryness
  5. customgiving 18 g of a highly viscous, pale yellow residue
  6. customa white solid precipitating out
  7. filtrationfiltered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-064cf11979be47df9e88b23ac3dd1a7b
Source dataset
uspto-grants-1992_05
Patent number
US05110983

Reaction notes

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