p-Toluenesulfonic acid → HCID 11821668, compound

HRID 638523Notes

Reaction equation

HRID 638523 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:27](O)[CH2:28][CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][CH2:27][O:8][C:7](=[O:9])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74333,5-Dinitrobenzoic acidHCID 104421,3-Propanediol

Product 1

HCID 11821668HCID 11821668, compoundYield 77%

Conditions

Temperature
110 °C

Procedure

A mixture of 30 g 3,5-dinitrobenzoic acid, 0.8 g p-toluenesulfonic acid and 100 ml 1,3-propanediol was stirred 9 hours at 110° C. After cooling, a white product crystallized and was separated from solution by filtration after adding a large quantity of water. The product was recrystallized from methanol to provide 77% white crystals with m.p. 76° C. IR: 1712 cm-1 (carbozyl) 1535 cm-1 (nitro asymmetric), 1341 cm-1 (nitro symmetric). 1H-NMR (DMSOd6): 9.05 ppm (C4), 8.93 ppm (C2, C6), 4.47 ppm (CH2OCO, triplet) 3.62 ppm (CH2O, triplet), 1.94 ppm (CH2 multiplet).

Workup

  1. temperatureAfter cooling
  2. customa white product crystallized
  3. customwas separated from solution by filtration
  4. additionafter adding a large quantity of water
  5. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-6629be25f4434c0ea3fc46830a2bd3f1
Source dataset
uspto-grants-1985_12
Patent number
US04562133

Reaction notes

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