Water → (E)-3-(3-methylphenyl)-1-(4-nitrophenyl)prop-2-en-1-one

HRID 330573Notes

Reaction equation

HRID 330573 reaction equation
B(O)(O)O.[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:16].O>C1(C)C(C)=CC=CC=1>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15](/[CH:14]=[CH:5]/[C:6]2[CH:13]=[CH:12][CH:11]=[C:8]([CH3:9])[CH:7]=2)=[O:16])=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7487p-NitroacetophenoneHCID 7628Boric Acid2×HCID 121053-Methylbenzaldehyde

Product 1

HCID 5780399(E)-3-(3-methylphenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10 g of boric acid are added to a solution of 76 g (0.63 mole) of 3-methylbenzaldehyde and 104.5 (0.63 mole) of 4-nitroacetophenone in 1 l of xylene, and the mixture is refluxed for 8 hours under a water separator. A further 5 g of boric acid are added, after which the mixture is boiled for a further 8 hours. This process is repeated until the theoretical amount of water has been separated off (2-3 times). The cooled reaction mixture is filtered under suction and the residue is washed with toluene and dried under reduced pressure to give 131 g (77% of theory) of a yellowish brown powder of melting point 130°-132° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours under a water separator
  2. customhas been separated off (2-3 times)
  3. customThe cooled reaction mixture
  4. filtrationis filtered under suction
  5. washthe residue is washed with toluene
  6. customdried under reduced pressure
  7. customto give 131 g (77% of theory) of a yellowish brown powder of melting point 130°-132° C.

Sources & evidence

ORD record
ord-4bccd0d17c5241b6bbb0687493df3be7
Source dataset
uspto-grants-1990_01
Patent number
US04897425

Reaction notes

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