Nitric Acid → HCID 13066911, compound

HRID 1074573Notes

Reaction equation

HRID 1074573 reaction equation
O1CCOCC1.C[O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19]C)=[C:11]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][C:30]#[C:31][CH2:32][OH:33])[C:10]=1[CH3:34].[N+]([O-])(O)=O>[Ag]=O.O>[CH3:34][C:10]1[C:9](=[O:8])[C:18]2[C:13]([C:12](=[O:19])[C:11]=1[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][C:30]#[C:31][CH2:32][OH:33])=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 312751,4-DioxaneHCID 13066910HCID 13066910, compound

Product 1

HCID 13066911HCID 13066911, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

Dioxane (15 ml) was added to 1,4-dimethoxy-2-methyl-3-[(12-hydroxy-5,10-dodecadiynyl)]naphthalene (II, 0.57 g, 1.5 mmole) and silver oxide (0.74 g, 6.0 mmole), and the mixture was stirred under cooling with ice. 6 N nitric acid (1.5 ml) was added to the mixture over a 5-minute period and, 5 minutes later, the ice bath was taken off, followed by stirring at room temperature for 30 minutes. Water (20 ml) was added to the reaction solution, and the dioxane was distilled off under reduced pressure. Ethyl acetate (50 ml) was added to the residue, and the insolubles were filtered out. The organic layer was separated out, washed with water and dried (over MgSO4), followed by distilling off the solvent under reduced pressure. The crystals precipitated were recrystallized from isopropyl ether, thereby yielding the desired 2-methyl-3-(12-hydroxy-5,10-dodecadiynyl)-1,4-naphthoquinone (I, 0.47 g, 90%).

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 30 minutes
  3. distillationthe dioxane was distilled off under reduced pressure
  4. additionEthyl acetate (50 ml) was added to the residue
  5. filtrationthe insolubles were filtered out
  6. customThe organic layer was separated out
  7. washwashed with water
  8. dry with materialdried (over MgSO4)
  9. distillationby distilling off the solvent under reduced pressure
  10. customThe crystals precipitated
  11. customwere recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-35249ce76ea9412bb6281665ea0c1071
Source dataset
uspto-grants-1983_07
Patent number
US04393075

Reaction notes

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