Water → HCID 53699063, compound

HRID 1679070Notes

Reaction equation

HRID 1679070 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.[OH2:23].[CH2:24]([O:26][C:27]([C:29]1[O:30][C:31]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)=[C:32]2[C:37]=1[CH:36]=[CH:35][CH:34]=[CH:33]2)=[O:28])[CH3:25]>C(O)(=O)C>[CH2:24]([O:26][C:27](=[O:28])[C:29]([C:37]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:31](=[O:30])[C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)=[O:23])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 9869224Ammonium cerium (IV) nitrateHCID 53839738Ethyl 3-(4-chlorophenyl)-2-benzofuran-1-carboxylate

Product 1

HCID 53699063HCID 53699063, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

11.5 G. of cerium (IV) ammonium nitrate are dissolved in 20 ml. of water and 20 ml. of glacial acetic 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-b593d72c65074d17a5dad06f363b9ce6
Source dataset
uspto-grants-1978_03
Patent number
US04077978

Reaction notes

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