Nitric Acid → HCID 15614968, compound

HRID 1088551Notes

Reaction equation

HRID 1088551 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:24])[C:15]=1[C:25]([F:28])([F:27])[F:26]>O>[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([N+:8]([O-:11])=[O:9])[C:20]=2[CH3:24])[C:15]=1[C:25]([F:26])([F:28])[F:27]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 155687612-Methoxy-5-methyl-1-(trifluoromethyl)naphthalene

Product 1

HCID 15614968HCID 15614968, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled solution (3° to 4° C.) of acetic anhydride (640 mL) was added fuming nitric acid (90%, specific gravity=1.5, 160 mL) dropwise via an addition funnel at such a rate as to keep the internal temperature at or below 8° C. (~1 hour 20 minutes total addition time). After the internal temperature had again cooled to 3°-4° C., 2-methoxy-5-methyl-1-trifluoromethylnaphthalene (200 g, 0.833 mol) was added portion wise. The portions added were small enough such that the internal temperature did not rise above 10° C. and each portion was added when the temperature had cooled to 5° C. (addition time ~1 hour 15 minutes). After an additional 15 minutes the reaction mixture was added to water (3 L). The resulting amorphous solid was filtered, washed with water and the lumps broken up and dried in vacuo overnight. The dry solid (~225 g) was recrystallized from 95:5 ethanol:isopropanol (3 L). The resulting long yellow needles were filtered and washed with ethanol (2×50 mL) to provide the product (97.5 g, 41%), m.p. 141°-142° C. A small amount of the desired product was recrystallized from 4:1 petroleum ether:ethyl acetate.

Workup

  1. custombelow 8° C. (~1 hour 20 minutes total addition time)
  2. temperatureAfter the internal temperature had again cooled to 3°-4° C.
  3. additionThe portions added
  4. customdid not rise above 10° C.
  5. additioneach portion was added when the temperature
  6. addition(addition time ~1 hour 15 minutes)
  7. filtrationThe resulting amorphous solid was filtered
  8. washwashed with water
  9. customdried in vacuo overnight
  10. customThe dry solid (~225 g) was recrystallized from 95:5 ethanol
  11. filtrationThe resulting long yellow needles were filtered
  12. washwashed with ethanol (2×50 mL)

Sources & evidence

ORD record
ord-63a40b24d0f543349eb734de17b5db5b
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

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