Nitric Acid → HCID 13850047, compound

HRID 1722050Notes

Reaction equation

HRID 1722050 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[CH2:7][CH:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15].O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[CH2:7][CH:8]([CH3:12])[O:9]2)=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 14773381HCID 14773381, compound

Product 1

HCID 13850047HCID 13850047, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

7-Chloro-2-methylchroman-4-one (4.56 g, 23.2 mmol) was dissolved in 7 ml concentrated sulfuric acid at 0°-5° C. and cooled in an acetone-ice bath. Nitric acid (1.41 ml, s.g. 1.5, 90%) in 3 ml concentrated sulfuric acid was added dropwise over 20 minutes. The resulting viscous mixture was poured into 150 ml ice and water and extracted with 200 ml ethyl acetate. The organic layer was separated, washed 4×50 ml water and then brine, dried over magnesium sulfate, and stripped to a tan solid, 5.8 g. The latter was chromatographed on 500 cc silica gel, initially eluting with 5 liters 1:10 diethyl ether:hexane to remove starting material and then with 5 liters of 1:5 diethyl ether:hexane to obtain title product as a white solid, 2 g (36%); m/e 241(P+), 226, 199, 183, 169, 154, 141. 1H-NMR indicates contamination with about 44% of the 7-chloro-8-nitro isomer.

Workup

  1. temperaturecooled in an acetone-ice bath
  2. extractionextracted with 200 ml ethyl acetate
  3. customThe organic layer was separated
  4. washwashed 4×50 ml water
  5. dry with materialbrine, dried over magnesium sulfate
  6. customThe latter was chromatographed on 500 cc silica gel
  7. washinitially eluting with 5 liters 1:10 diethyl ether
  8. customhexane to remove

Sources & evidence

ORD record
ord-2899585dbb4f4cec98a76009355fdb87
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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