Nitric Acid → HCID 2752760, compound

HRID 362671Notes

Reaction equation

HRID 362671 reaction equation
[C:1]1(=[O:9])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2]1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16]>O>[N+:15]([C:8]1[C:3]2[CH2:2][C:1](=[O:9])[C:4]=2[CH:5]=[CH:6][CH:7]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 137953Benzocyclobutenone

Product 1

HCID 2752760HCID 2752760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzocyclobutenone (1.20 g) was added slowly to concentrated sulfuric acid (5 mL) at 0° C. with vigorous stirring. The mixture of concentrated sulfuric acid (1.0 mL) and nitric acid (70%, 1.05 g) was added at such a rate that the solution temperature remained at 10° C. After the completion of addition of nitrating solution, the reaction mixture was then poured into icey water (30 mL). The resulting mixture was filtered. The filtrate was neutralized with sodium carbonate powders and the water was then evaporated under vacuum. The residue was then extracted with methylene chloride (3×50 mL). After removal of methylene chloride, the pure product (3-nitrobenzocyclobutenone) was isolated from the residue by chromatography on silica gel: 55 mg; IR (KBr) 1349, 1525, 1772 cm-1 ; 1H NMR (200 MHz, CDCl3) 4.42 (s, 2H), 7.68 (m, 2H), 8.31 (m, 1H); MS (EI, m/e, relative intensity %) 164 (M+. +H, 2.5), 135 (M+. -CO, 10.3), 89 (135 -.NO2, 38).

Workup

  1. additionwas added at such a rate that the solution temperature
  2. customremained at 10° C
  3. additionAfter the completion of addition of nitrating solution
  4. filtrationThe resulting mixture was filtered
  5. customthe water was then evaporated under vacuum
  6. extractionThe residue was then extracted with methylene chloride (3×50 mL)
  7. customAfter removal of methylene chloride

Sources & evidence

ORD record
ord-abcd626523124f97a403eebc11b12567
Source dataset
uspto-grants-1999_02
Patent number
US05869693

Reaction notes

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