Diethylene Glycol → 4,5-Dinitro-2-[beta-(2-hydroxyethoxy)ethoxy]phenol

HRID 2051039Notes

Reaction equation

HRID 2051039 reaction equation
[OH-].[K+].[CH2:3]([OH:9])[CH2:4][O:5][CH2:6]CO.[CH2:10]1[O:18][C:17]2[C:12](=[CH:13][C:14]([N+:22]([O-:24])=[O:23])=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=2)[O:11]1>C(O)(=O)C>[N+:19]([C:15]1[C:14]([N+:22]([O-:24])=[O:23])=[CH:13][C:12]([OH:11])=[C:17]([O:18][CH2:10][CH2:6][O:5][CH2:4][CH2:3][OH:9])[CH:16]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 6113255,6-Dinitro-1,3-benzodioxole

Product 1

HCID 137508624,5-Dinitro-2-[beta-(2-hydroxyethoxy)ethoxy]phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.4 mol (26.4g) of 85% pure potassium hydroxide pellets is added at 70° C. to 200 ml of diethylene glycol. 0.2 mol (42 4g) of 4,5-methylenedioxy-1,2-dinitrobenzene is added to this solution. The heating is maintained for 31/2 hours After dilution with ice-cold water and neutralization with 22 ml of acetic acid, the expected product precipitates. After being dried, it is recrystallized from 96° strength alcohol. It melts at 135° C. Analysis of the product gives the following results:

Workup

  1. customthe expected product precipitates
  2. customAfter being dried
  3. customit is recrystallized from 96° strength alcohol
  4. customAnalysis of the product gives the
  5. customfollowing results

Sources & evidence

ORD record
ord-a4e91c35899844ebb76f966598c6f5a9
Source dataset
uspto-grants-1991_05
Patent number
US05015769

Reaction notes

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