Toluene → Benzophenone

HRID 1404819Notes

Reaction equation

HRID 1404819 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[Na+].CS[C:9]1[CH:14]=[CH:13][CH:12]=[C:11](SC)C=1.[C:17]1(C)[CH:22]=[CH:21]C=[CH:19][CH:18]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)[C-]2C=CC=C2CCP(C(C)(C)C)C(C)(C)C)CCCCC1.[CH-]1C=CC=C1.[Fe+2]>[C:2]([C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1)(=[O:4])[C:1]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 137576Benzene, 1,3-bis(methylthio)-HCID 23676156Sodium t-butoxide

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 178454874HCID 178454874, compoundCatalyst

Procedure

The above compound of the formula (32), 13.7 g (142.8 mmol) of sodium-t-butoxide, 0.7 g (1.3 mmol) of bis(dibenzylideneacetone)palladium, 1.75 g (1.3 mmol) of 1-dicyclohexylphosphino-2-di-t-butylphosphinoethyl ferrocene and 17.9 g (129.8 mmol) of 2,6-dimethylthiobenzene were dissolved in 400 ml of toluene in an argon atmosphere and refluxed for 3 hours. After a reaction, the reaction solution was washed with water, the solvent was removed, and the obtained product was purified by column chromatography to obtain a benzophenone derivative represented by the following formula (33) as 41.1 g (118.1 mmol, yield of 91%) of a white solid.

Workup

  1. temperaturerefluxed for 3 hours
  2. customAfter a reaction
  3. washthe reaction solution was washed with water
  4. customthe solvent was removed
  5. customthe obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-08c2e964d21341c2b3ee6cd03fa2c14b
Source dataset
uspto-grants-2014_12
Patent number
US08916071B2

Reaction notes

Loading…