Nitric Acid → HCID 18414060, compound

HRID 428518Notes

Reaction equation

HRID 428518 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][CH2:10][CH2:9]2>C(OC(=O)C)(=O)C>[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([N+:1]([O-:4])=[O:2])[CH:15]=1)[O:12][CH2:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 114691696-fluorochroman

Product 1

HCID 18414060HCID 18414060, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

A mixture of nitric acid (100%, 7.8 ml, 0.16 mol) in acetic anhydride was maintained at room temperature for 0.5 hour. This mixture was added to a solution of 6-fluorochroman (11.9 g, 0.078 mol) in 40 ml acetic anhydride at 0C. The reaction mixture was stirred at room temperature for 2 hours then poured into ice-water. The mixture was extracted with methylene chloride (3×60 ml) and washed with saturated sodium carbonate (8×150 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford a yellow solid: mp 48-50° C.

Workup

  1. extractionThe mixture was extracted with methylene chloride (3×60 ml)
  2. washwashed with saturated sodium carbonate (8×150 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum
  6. customto afford a yellow solid

Sources & evidence

ORD record
ord-e3dd39d82c7a456aad1457a52658dd34
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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