Benzene → 1,6-Diphenyl-1,6-hexanedione

HRID 1377220Notes

Reaction equation

HRID 1377220 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11].[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 61034Adipoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 769031,6-Diphenyl-1,6-hexanedione

Procedure

In a 2-liter three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 700 milliliters of benzene was introduced and 177.0 g of aluminum chloride was added with ice cooling. Then, a solution of 101.6 g of adipoyl chloride in 300 milliliters of benzene was added dropwise for 35 minutes. After stirring for one day and one night with warming back to the room temperature, the solution was poured in 3 liters of ice water containing dilute hydrochloric acid, and extracted with 2.5 liters of toluene. Thereafter, the solution was washed with a 0.5N aqueous solution of sodium hydroxide and water, and then dried with anhydrous magnesium sulfate. After removing off the solvent by a rotary evaporator, 128.4 g of 1,6-diphenylhexane-1,6-dione was obtained as crystals by recrystallizing the obtained crystals from ethyl acetate.

Workup

  1. customIn a 2-liter three-necked flask equipped with a stirring device
  2. extractionextracted with 2.5 liters of toluene
  3. washThereafter, the solution was washed with a 0.5N aqueous solution of sodium hydroxide and water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customAfter removing off the solvent
  6. customby a rotary evaporator

Sources & evidence

ORD record
ord-054ecf1c5ed241dabb0e76861f2a6182
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

Loading…