1,3-Propanediol → HCID 19751957, compound

HRID 2051067Notes

Reaction equation

HRID 2051067 reaction equation
[N+:1]([C:4]1[C:5](Cl)=[C:6]([Cl:14])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1Cl)([O-:3])=[O:2].[OH-:16].[K+].[CH2:18]([OH:22])[CH2:19][CH2:20][OH:21]>>[N+:1]([C:4]1[C:5]([O:16][CH2:18][CH2:19][CH2:20][OH:21])=[C:6]([Cl:14])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:21][CH2:20][CH2:19][CH2:18][OH:22])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 104421,3-Propanediol2×HCID 14797Potassium HydroxideHCID 175841,2,4-Trichloro-3,5-dinitrobenzene

Product 1

HCID 19751957HCID 19751957, compound

Conditions

Temperature
85 °C

Procedure

1 mole (271.5 g) of 3,5-dinitro-1,2,4-trichlorobenzene in 700 ml of 1,3-propanediol was heated to 85° C. 2 moles of powdered potassium hydroxide dissolved in 280 ml of 1,3-propanediol were added over 30 minutes. The reaction mixture was heated for 1 hour at 85° C. upon completion of the additions. After cooling, the expected product was filtered off, washed with water and then dissolved in 1.5 litres of ethyl acetate which, after washing with water, was dried over sodium sulphate. Upon concentration to dryness, a precipitate was obtained which, after having recrystallized from isopropyl ether, melted at 90° C.

Workup

  1. additionwere added over 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe expected product was filtered off
  4. washwashed with water
  5. dissolutiondissolved in 1.5 litres of ethyl acetate which
  6. washafter washing with water
  7. dry with materialwas dried over sodium sulphate
  8. concentrationUpon concentration to dryness
  9. customa precipitate was obtained which
  10. customafter having recrystallized from isopropyl ether, melted at 90° C.

Sources & evidence

ORD record
ord-acf11bc5d6c042ee8eec37aef39a0599
Source dataset
uspto-grants-1991_05
Patent number
US05015772

Reaction notes

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