Nitric Acid → HCID 66745352, compound

HRID 1175761Notes

Reaction equation

HRID 1175761 reaction equation
[O:1]=[C:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3]1.OS(O)(=O)=O.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[N+:20]([C:12]1[CH:13]=[CH:14][C:9]2[O:8][C:4]3([CH2:7][CH2:6][CH2:5]3)[CH2:3][C:2](=[O:1])[C:10]=2[CH:11]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 58237899spiro[chroman-2,1'-cyclobutan]-4-one

Product 1

HCID 66745352HCID 66745352, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3,4-Dihydro-4-oxo-spiro[2H-1-benzopyran-2,1′-cyclobutane] (Example 3) (10 mmol) in glacial acetic acid (2 ml), conc. H2SO4 (10 mmol) was added at 0° C. and the mixture was stirred for 10 min. A chilled nitrating mixture [prepared from HNO3 (9 mmol) and Conc. H2SO4 (10 mmol)] was then added very slowly and the reaction mixture was allowed to warm up to room temperature and stirred for 5 h. reaction mixture was then quenched with water and the compound was extracted in dichloromethane. Organic layer was separated, dried on anhydrous MgSO4 and concentrated under vacuum. The crude product was then purified by column chromatography to afford the desired compound as a yellow solid.

Workup

  1. additionwas then added very slowly
  2. stirringstirred for 5 h.
  3. customreaction mixture
  4. customwas then quenched with water
  5. extractionthe compound was extracted in dichloromethane
  6. customOrganic layer was separated
  7. dry with materialdried on anhydrous MgSO4
  8. concentrationconcentrated under vacuum
  9. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-8cdd20c896ac430e849544ca62a77598
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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