Potassium Carbonate → 7-[(4-Nitrophenyl)methoxy]-3-phenylchromen-4-one

HRID 1862864Notes

Reaction equation

HRID 1862864 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]I)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:18])[C:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:8][O:9]3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76598alpha-Iodo-p-nitrotolueneHCID 53768917-Hydroxyisoflavone

Product 1

HCID 15228077-[(4-Nitrophenyl)methoxy]-3-phenylchromen-4-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.5 g of 7-hydroxy-isoflavone in 200 ml of anhydrous acetone are boiled for 2 hours with 11.8 g of p-nitrobenzyl iodide in the presence of 5.7 g of anhydrous potassium carbonate under reflux condenser. On distilling off about half of the volume of acetone, the residue is poured onto 1000 ml of water. The precipitating crude product is subjected to suction and recrystallized from glacial acetic acid, affording light yellow plates of 7-p-nitrobenzyloxy-isoflavone, m.p. 225°-226° C.

Workup

  1. temperatureunder reflux condenser
  2. distillationOn distilling off about half of the volume of acetone
  3. additionthe residue is poured onto 1000 ml of water
  4. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-a61f1c4e9df04bcb8c154ed451741622
Source dataset
uspto-grants-1979_09
Patent number
US04166862

Reaction notes

Loading…