Ethylene Glycol → HCID 19915466, compound

HRID 1089623Notes

Reaction equation

HRID 1089623 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH2:18]([OH:21])[CH2:19][OH:20].[OH-].[Na+]>O>[OH:20][CH2:19][CH2:18][O:21][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium Hydroxide3×HCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-

Product 1

HCID 19915466HCID 19915466, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

27 g of 4-chloro-5-trifluoromethyl-1,3-dinitrobenzene are initially introduced into 37 g of ethylene glycol, and 11.4 g of 50 percent strength aqueous sodium hydroxide solution are added dropwise at 45° C. in the course of 20 minutes. The mixture is subsequently stirred at 45° C. for 1 hour, a further 1.5 g of sodium hydroxide solution are added, the mixture is subsequently stirred at 45° C. for 1 hour, a furthere 1.5 g of sodium hydroxide solution are added, the mixture is subsequently stirred at 45° C. for a further hour and 200 ml of water are then added. The oil which has separated out is separated off, washed twice with 30 ml of water each time and dissolved in 75 ml of ethyl acetate and the solution is washed again with water. The ethyl acetate phase is then dried and concentrated.

Workup

  1. additionare added dropwise at 45° C. in the course of 20 minutes
  2. stirringthe mixture is subsequently stirred at 45° C. for 1 hour
  3. stirringthe mixture is subsequently stirred at 45° C. for a further hour
  4. customThe oil which has separated out
  5. customis separated off
  6. washwashed twice with 30 ml of water each time
  7. dissolutiondissolved in 75 ml of ethyl acetate
  8. washthe solution is washed again with water
  9. dry with materialThe ethyl acetate phase is then dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-021e024ac0c243a0950047b1d040f8d5
Source dataset
uspto-grants-1992_01
Patent number
US05078748

Reaction notes

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