Ethanol → HCID 21962448, compound

HRID 971427Notes

Reaction equation

HRID 971427 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.C([O:18][C:19](=[O:25])[C:20](OCC)=[O:21])C>O>[N+:13]([C:8]1[CH:7]=[C:6]([Cl:5])[CH:11]=[CH:10][C:9]=1[CH2:12][C:20](=[O:21])[C:19]([OH:25])=[O:18])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6975Benzene, 4-chloro-1-methyl-2-nitro-HCID 7268Diethyl OxalateHCID 5360545Sodium

Product 1

HCID 21962448HCID 21962448, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled mixture prepared by adding 13.6 g. of sodium to 300 ml. of ethanol is added a solution of 100 g. of 4-chloro-2-nitrotoluene and 84 g. of diethyloxalate in 150 ml. of ethanol while maintaining the temperature below 20° C. The resulting mixture is refluxed for one hour, cooled, 400 ml. of water added and the resulting mixture refluxed for 90 minutes. The ethanol is then evaporated to a small volume and the resulting precipitate contains tan and black material and the black material is mechanically separated and discarded and the remainder (filtrate plus tan precipitate) used in the next step.

Workup

  1. customTo a cooled mixture prepared
  2. additionby adding 13.6 g
  3. temperatureThe resulting mixture is refluxed for one hour
  4. temperaturecooled
  5. temperaturethe resulting mixture refluxed for 90 minutes
  6. customThe ethanol is then evaporated to a small volume
  7. customblack material and the black material is mechanically separated

Sources & evidence

ORD record
ord-2459b4650b8e4ba386a069400ca15ff5
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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