Nitric Acid → 1,1,2,3,3,5-Hexamethyl-6-nitro-2,3-dihydro-1H-indene

HRID 1906355Notes

Reaction equation

HRID 1906355 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([CH3:13])([CH3:12])[CH:3]1[CH3:14].[N+:16]([O-])([OH:18])=[O:17].S(=O)(=O)(O)O>C(O)(=O)C>[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:16]([O-:18])=[O:17])=[C:8]([CH3:11])[CH:9]=2)[C:4]([CH3:13])([CH3:12])[CH:3]1[CH3:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 955201H-Indene, 2,3-dihydro-1,1,2,3,3,5-hexamethyl-

Product 1

HCID 198103681,1,2,3,3,5-Hexamethyl-6-nitro-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a 500 ml reaction vessel equipped with stirrer, thermometer, reflux condensor, addition funnel and cooling bath is placed 51 grams of 1,1,2,3,3,6-hexamethyl indane having the structure: ##STR40## (51 grams) in admixture with 100 grams of acetic acid. The resulting mixture is cooled to 10° C. Over a period of 0.5 hours, 40 grams of fuming nitric acid is added to the reaction mass, while maintaining the reaction mass at 10° C. Over a period of 10 minutes, 10 grams of concentrated sulfuric acid is then added to the reaction mass. The reaction mass is then heated to 25° C. and maintained at 25° C. for a period of 3.5 hours. At the end of the 3.5 hour period, the reaction mass is quenched with ice water (500 ml) and crystals are formed. The crystals are then re-crystallized from water. The melting point of the resulting crystals is 115.7° C. NMR, IR and mass spectral anaylses yield the information that the compound has the structure: ##STR41##

Workup

  1. customTo a 500 ml reaction vessel
  2. customequipped with stirrer
  3. temperaturethermometer, reflux
  4. additioncondensor, addition funnel
  5. temperaturecooling bath
  6. temperaturewhile maintaining the reaction mass at 10° C
  7. waitOver a period of 10 minutes
  8. temperatureThe reaction mass is then heated to 25° C.
  9. temperaturemaintained at 25° C. for a period of 3.5 hours
  10. customAt the end of the 3.5 hour period, the reaction mass is quenched with ice water (500 ml) and crystals
  11. customare formed
  12. customThe crystals are then re-crystallized from water
  13. customis 115.7° C
  14. customNMR, IR and mass spectral anaylses yield the information that the compound

Sources & evidence

ORD record
ord-09773ba479264bc08ea1b52f262ff562
Source dataset
uspto-grants-1987_03
Patent number
US04652400

Reaction notes

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