Ammonium cerium (IV) nitrate → HCID 53699063, compound

HRID 372325Notes

Reaction equation

HRID 372325 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=[O:20].[CH2:23]([O:25][C:26]([C:28]1[O:29][C:30]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)=[C:31]2[C:36]=1[CH:35]=[CH:34][CH:33]=[CH:32]2)=[O:27])[CH3:24]>O>[CH2:23]([O:25][C:26](=[O:27])[C:28]([C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:30](=[O:29])[C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)=[O:20])[CH3:24]

Participants

4

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 53839738Ethyl 3-(4-chlorophenyl)-2-benzofuran-1-carboxylate

Product 1

HCID 53699063HCID 53699063, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.5 G. of cerium (IV) ammonium nitrate are dissolved in 20 ml. of water and 20 ml. of glacial acid. Thereafter, there are added 3.0 g. of 3-(p-chlorophenyl)-isobenzofuran-1-carboxylic acid ethyl ester and the mixture is boiled for 2-3 minutes until the color of the solution obtained changes from orange to light-yellow. After cooling, there are added 150 ml. of ice-water and the mixture is stirred for 1 hour in an ice-bath. The product which first separates as an oil solidifies. The solid is separated by decantation of the aqueous solution and is dissolved in ether. The ethereal solution is washed with 2-N sodium carbonate and water, dried over sodium sulfate and evaporated. After crystallization of the residue from ethanol, there is obtained [o-(p-chlorobenzoyl)-phenyl]glyoxylic acid ethyl ester in the form of colorless crystals having a melting point of 79°-81° C.

Workup

  1. additionThereafter, there are added 3.0 g
  2. customobtained changes from orange to light-yellow
  3. temperatureAfter cooling
  4. additionthere are added 150 ml
  5. customThe solid is separated by decantation of the aqueous solution
  6. dissolutionis dissolved in ether
  7. washThe ethereal solution is washed with 2-N sodium carbonate and water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customAfter crystallization of the residue from ethanol

Sources & evidence

ORD record
ord-cd8ab2cc8d314d7e9514176dc92ca9b1
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

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