Ethylene Glycol → HCID 53976298, compound

HRID 1285266Notes

Reaction equation

HRID 1285266 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C=C.[Na].C(OCC)(=O)C.[CH2:24]([OH:27])[CH2:25][OH:26]>>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[O:26][CH2:25][CH2:24][OH:27]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 86740622HCID 86740622, compound

Product 1

HCID 53976298HCID 53976298, compound

Procedure

94.8 g (0.40 moles) 1,5-dichloro-2,4-dinitrobenzene in 580 ml ethylene glycol is heated to 50° C. To the mixture is then very gradually added, with stirring, 50.4 g (0.60 moles) sodium ethylene glycoxide over approximately 6 hours. One hour after addition is complete, TLC (ethyl acetate) shows the reaction is complete. The heat is turned off and the mixture is allowed to cool to room temperature. The precipitated product is collected by vacuum filtration and is washed with water. The water causes additional product to precipitate in the filtrate. The product is dried in a vacuum oven at 50° C. Yield of the combined crops is 82.7 g (78.8%), m.p. 98°-100° C.

Workup

  1. additionTo the mixture is then very gradually added
  2. additionOne hour after addition
  3. filtrationThe precipitated product is collected by vacuum filtration
  4. washis washed with water
  5. customto precipitate in the filtrate
  6. customThe product is dried in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-0c55175b4d1441d3bc069dc38ea31997
Source dataset
uspto-grants-1986_01
Patent number
US04566876

Reaction notes

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