Ethanol → HCID 13409053, compound

HRID 2166851Notes

Reaction equation

HRID 2166851 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]#N.[CH2:22]([OH:24])[CH3:23].[OH:25]S(O)(=O)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([O:24][CH2:22][CH3:23])=[O:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13409052HCID 13409052, compound

Product 1

HCID 13409053HCID 13409053, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,3-dichloro-4-(p-nitrophenoxy)phenyl acetonitrile (from Example 29) (6.5 g., 0.02 mole) in 15 ml. of 95% ethanol was added 5 ml. of concentrated H2SO4. The solution was refluxed for 24 hours. The ethanol was evaporated and the residue was diluted with water. The aqueous mixture was extracted with chloroform. The organic solution was washed with brine, dried over Na2SO4 and evaporated to provide 6.9 g. of the desired ethyl ester. NMR (CDCl3): 3.87 (2H, s, ArCH2CO2Et); IR (CHCl3) 1730 cm-1.

Workup

  1. temperatureThe solution was refluxed for 24 hours
  2. customThe ethanol was evaporated
  3. additionthe residue was diluted with water
  4. extractionThe aqueous mixture was extracted with chloroform
  5. washThe organic solution was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto provide 6.9 g

Sources & evidence

ORD record
ord-1355e7ac27fc4091b38df7ba17b23776
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

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