Toluene → 2,2-Bis(4-methylphenyl)hexafluoropropane

HRID 1649961Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=O.F.[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:18][C:12]1[CH:17]=[CH:16][C:15]([C:3]([C:15]2[CH:16]=[CH:17][C:12]([CH3:18])=[CH:13][CH:14]=2)([C:5]([F:8])([F:7])[F:6])[C:2]([F:10])([F:9])[F:1])=[CH:14][CH:13]=1

Participants

Reactant 3

HCID 1140Toluene

HCID 12695Hexafluoroacetone

HCID 14917Hydrofluoric Acid

Product 1

HCID 6219312,2-Bis(4-methylphenyl)hexafluoropropane

Procedure

It has been disclosed in U.S. Pat. No. 3,310,573 to react toluene with hexafluoroacetone in the presence of hydrofluoric acid to give 2,2-bis-(4-methylphenyl)hexafluoropropane (2). This is oxidized to the dicarboxylic acid (3) using chromium(III) oxide, which is subsequently converted into the 2,2-bis-(4-aminophenyl)hexafluoropropane (4) by a Schmidt reaction using sodium azide/sulfuric acid. In the next reaction steps, this compound is acetylated using acetic anhydride and then nitrated in the 3-position using 70% strength nitric acid in concentrated sulfuric acid. The elimination of the acetyl group then takes place, for which the nitrated substance is dissolved in concentrated sulfuric acid and water added until the 2,2-bis-(3-nitro-4-aminophenyl)hexafluoropropane (5) precipitates from the solution.

Sources & evidence

ORD record: ord-7028e56870094d91bf62b253a2508553
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04922019

Reaction notes

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