Trifluoroacetic acid → 2(3H)-Benzofuranone, 5,7-bis(1,1-dimethylethyl)-3-(3,4-dimethylphenyl)-

HRID 2228818Notes

Reaction equation

HRID 2228818 reaction equation
[C:1]([C:5]1[C:6](=[O:24])[C:7](=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)[C:27](O)=[O:28]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]2[O:24][C:27](=[O:28])[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([CH3:23])[CH:17]=3)[C:7]=2[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54529216HCID 54529216, compound2×

Product 1

HCID 99503072(3H)-Benzofuranone, 5,7-bis(1,1-dimethylethyl)-3-(3,4-dimethylphenyl)-Yield 66%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 645 mg (2.0 mmol) of a mixture of 2,4-di-tert-butyl-6-(3,4-dimethyl-benzylidene)-cyclohexa-2,4-dienone (compound (301). Table 3) and the corresponding dimer (compound (401), Table 4), prepared according to Example 1b, in 7 ml of toluene is degassed using argon and then 58 mg (0.05 mmol) of tetrakis(triphenylphosphine)-palladium(0) and 23 mg (0.20 mmol) of trifluoroacetic acid are added. The autoclave is flushed with carbon monoxide and sealed, and a carbon monoxide pressure of 5 bar is then applied. The reaction mixture is maintained at 80° C. for 20 hours. After cooling to room temperature, the reaction mixture is poured into water and extracted three times using ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated using a vacuum rotary evaporator. Crystallisation of the residue from ethanol yields 464 mg (66%) of 5,7-di-tert-butyl-3-(3,4-dimethyl-phenyl)-3H-benzofuran-2-one (compound (101), Table 1), m.p. 130-132° C. Analysis, calculated: C 82.24; H 8.63%. Analysis, found: C 82.20; H 8.68%.

Workup

  1. customis degassed
  2. customThe autoclave is flushed with carbon monoxide
  3. customsealed
  4. temperatureAfter cooling to room temperature
  5. additionthe reaction mixture is poured into water
  6. extractionextracted three times
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customa vacuum rotary evaporator
  10. customCrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-3f332321514a4ba9a2acee03ea2ddf4e
Source dataset
uspto-grants-2002_07
Patent number
US06417358B1

Reaction notes

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