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

HRID 649653Notes

Reaction equation

HRID 649653 reaction equation
[OH-].[K+].[CH2:3]1[O:11][C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=2)[O:4]1.[CH2:18]([OH:24])[CH2:19][O:20][CH2:21]CO>>[N+:12]([C:8]1[C:7]([N+:15]([O-:17])=[O:16])=[CH:6][C:5]([OH:4])=[C:10]([O:11][CH2:3][CH2:21][O:20][CH2:19][CH2:18][OH:24])[CH:9]=1)([O-:14])=[O:13]

Participants

4

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

Procedure

0.4 mol (26.4 g) of 85% pure potassium hydroxide pellets is added at 70° C. to 200 ml of diethylene glycol. 0.2 mol (42.4 g) 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.

Workup

  1. temperatureThe heating is maintained for 31/2 hours
  2. customAfter dilution with ice-cold water and neutralization with 22 ml of acetic acid, the expected product precipitates
  3. customAfter being dried
  4. customit is recrystallized from 96° strength alcohol

Sources & evidence

ORD record
ord-ace5c3eeccb8417c831ac1b3b7524f7e
Source dataset
uspto-grants-1988_04
Patent number
US04740622

Reaction notes

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