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

HRID 1605177Notes

Reaction equation

HRID 1605177 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 anydrous potassium carbonate under a reflux condenser. On distilling off about half of the volume of acetone, the residue is poured into 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. distillationOn distilling off about half of the volume of acetone
  2. additionthe residue is poured into 1000 ml of water
  3. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-16f57ac4453e480490a98eddf4981b5f
Source dataset
uspto-grants-1976_04
Patent number
US03949085

Reaction notes

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