Acetophenone → 1,3-Propanedione, 1,1'-(1,4-phenylene)bis[3-phenyl-

HRID 2164655Notes

Reaction equation

HRID 2164655 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10]([O:22]C)(=O)[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=1.C([N-][CH:28]([CH3:30])[CH3:29])(C)C.[Li+]>CCOCC>[C:1]([CH2:2][C:15]([C:14]1[CH:13]=[CH:12][C:11]([C:10](=[O:22])[CH2:2][C:1](=[O:3])[C:29]2[CH:28]=[CH:30][CH:9]=[CH:4][CH:5]=2)=[CH:20][CH:19]=1)=[O:17])(=[O:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 8441Dimethyl terephthalateHCID 2724682Lithium diisopropylamide

Product 1

HCID 29095401,3-Propanedione, 1,1'-(1,4-phenylene)bis[3-phenyl-Yield 28%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 24.0 g (0.2 mol) of acetophenone and 19.4 g (0.1 mol) of dimethyl terephthalate in 150 ml of ether was dropwise added an ether solution of 0.4 mol of lithium diisopropylamide at -20° C. over 2 hours. After the dropwise addition, the mixture was stirred for 1 hour under cooling with ice, then poured into ice-water. After neutralization with an ammonium chloride aqueous solution, it was extracted with ether, and the extract was dried and concentrated. Recrystallization of the residue from methanol gave 9.5 g (28%) of the title compound. m.p. 175°-177° C.

Workup

  1. additionAfter the dropwise addition
  2. temperatureunder cooling with ice
  3. extractionAfter neutralization with an ammonium chloride aqueous solution, it was extracted with ether
  4. customthe extract was dried
  5. concentrationconcentrated
  6. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-07eabd4587c2445190d5766ab9ff90b8
Source dataset
uspto-grants-1985_03
Patent number
US04506001

Reaction notes

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