Ethanol → HCID 20296030, compound

HRID 1389942Notes

Reaction equation

HRID 1389942 reaction equation
C(O)C.[OH-].[Na+].C([N:8]([C:21]1[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[CH:23][C:22]=1[Cl:29])[CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:10]([OH:12])=[O:11])C>O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:9]([C:10]([OH:12])=[O:11])[NH:8][C:21]1[CH:26]=[C:25]([Cl:27])[C:24]([Cl:28])=[CH:23][C:22]=1[Cl:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70566809HCID 70566809, compound

Product 1

HCID 20296030HCID 20296030, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and refluxed solution of 40 parts of ethanol, 25 parts of water and 2 parts of sodium hydroxide are added 5 parts of ethyl 2-(o-methoxyphenyl)-N-(2,4,5-trichlorophenyl)glycine and stirring at reflux temperature is continued for 4 hours. The reaction mixture is evaporated. The residue is dissolved in 250 parts of water. The solution is shaken with 80 parts of ether and the aqueous phase is acidified with concentrated hydrochloric acid solution. The product is extracted twice with 80 parts of ether. The combined extracts are dried and evaporated. The solid residue is crystallized from 50 parts of glacial acetic acid at room temperature, yielding 3.2 parts of 2-(o-methoxyphenyl)-N-(2,4,5-trichlorophenyl)glycine; mp. 188.3° C.

Workup

  1. stirringstirring
  2. temperatureat reflux temperature
  3. customThe reaction mixture is evaporated
  4. dissolutionThe residue is dissolved in 250 parts of water
  5. stirringThe solution is shaken with 80 parts of ether
  6. extractionThe product is extracted twice with 80 parts of ether
  7. customThe combined extracts are dried
  8. customevaporated
  9. customThe solid residue is crystallized from 50 parts of glacial acetic acid at room temperature

Sources & evidence

ORD record
ord-978df96576e840118b03c3230c987ecf
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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