Hydrochloric Acid → 2-Nitroresorcinol ditosylate

HRID 647225Notes

Reaction equation

HRID 647225 reaction equation
[N+:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])([O-:3])=[O:2].C1(C)C(S([C:21]2([CH3:31])[CH:30]=[CH:29][C:24]([S:25](Cl)(=[O:27])=[O:26])=[CH:23][CH2:22]2)(=O)=O)=CC=CC=1.C(N([CH2:38][CH3:39])CC)C.Cl>C1COCC1>[S:25]([O:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:10]([O:11][S:25]([C:24]2[CH:23]=[CH:22][C:21]([CH3:31])=[CH:30][CH:29]=2)(=[O:26])=[O:27])[C:4]=1[N+:1]([O-:3])=[O:2])([C:39]1[CH:38]=[CH:30][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 117602-NitroresorcinolHCID 86739056p-Toluenesulfonyl(tosyl)chloride

Product 1

HCID 543037482-Nitroresorcinol ditosylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-nitroresorcinol (31.0 g, 0.2 mole) and p-toluenesulfonyl(tosyl) chloride (83.9 g, 0.44 mole) in THF (500 ml) at ≤15° C. was added triethylamine (84 ml, 0.6 mole) at such a rate that the temperature did not exceed 15° C. The mixture was stirred two additional hours at ambient temperature. The reaction was then poured into ice water (5 liters) and hydrochloric acid (100 ml) with stirring. The resulting precipitate was collected, air dried, and recrystallized from acetonitrile (250 ml) to yield 85.6 g (92.3 percent) of a white crystalline product. Thin layer chromatography (TLC) showed the product to be pure.

Workup

  1. customdid not exceed 15° C
  2. stirringwith stirring
  3. customThe resulting precipitate was collected
  4. customair dried
  5. customrecrystallized from acetonitrile (250 ml)

Sources & evidence

ORD record
ord-6905003233e34496a4247cf142bb4058
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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