Acetic Acid → 2-(4-Carboxyphenyl)-2-phenylhexafluoropropane

HRID 1975861Notes

Reaction equation

HRID 1975861 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21]C=[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.Br.[C:24]([OH:27])(=[O:26])[CH3:25]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>[C:24]([C:25]1[CH:21]=[CH:22][C:17]([C:8]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])=[CH:18][CH:19]=1)([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen Bromide2×HCID 147667062-(4-Methylphenyl)-2-phenylhexafluoropropane

Product 1

HCID 147667072-(4-Carboxyphenyl)-2-phenylhexafluoropropane

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 178476541HCID 178476541, compoundCatalyst

Conditions

Temperature
180 °C

Procedure

298 g of 2-(4-methylphenyl)-2-phenylhexafluoropropane, 2.49 g of cobalt(II) acetate tetrahydrate, 2.45 g of manganese(IV) acetate tetrahydrate and 0.41 g of hydrogen bromide (corresponding to 4.1 g of a 10% strength HBr solution in glacial acetic acid) were initially introduced into a 1 l glass autoclave. The mixture was heated to about 180° C. under an oxygen pressure of 6.5 bar and under an exothermic reaction and was left at 170°-180° C. for 1 hour. The reaction solution was cooled to about 100° C. and 200 g of acetic acid were then distilled off. 275 g of water were slowly added to the solution remaining in the flask (about 600 g) at the boiling point. The carboxylic acid which had crystallized out was filtered off with suction, washed twice with 75 ml of 50% strength aqueous acetic acid each time and five times with 85 ml of water each time and dried at 60° C./60 mbar. Yield: 311 g (95.5% of theory) melting point: 153°-155° C., small colorless crystals.

Workup

  1. customunder an exothermic reaction
  2. temperatureThe reaction solution was cooled to about 100° C.
  3. distillation200 g of acetic acid were then distilled off
  4. addition275 g of water were slowly added to the solution
  5. customThe carboxylic acid which had crystallized out
  6. filtrationwas filtered off with suction
  7. washwashed twice with 75 ml of 50% strength aqueous acetic acid each time and five times with 85 ml of water each time
  8. customdried at 60° C./60 mbar

Sources & evidence

ORD record
ord-1df8b80c3bce4765a3456ac59f467e1b
Source dataset
uspto-grants-1994_02
Patent number
US05288908

Reaction notes

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