Nitric Acid → 7-Nitro-1-tetralone

HRID 518843Notes

Reaction equation

HRID 518843 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>O>[N+:17]([C:6]1[CH:7]=[C:8]2[C:3]([CH2:2][CH2:1][CH2:11][C:9]2=[O:10])=[CH:4][CH:5]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 107241-Tetralone

Product 1

HCID 384457-Nitro-1-tetralone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

5 g of alpha-tetralone are added to 18.2 ml of sulfuric acid cooled to 0° C., while maintaining the temperature <10° C. A mixture of 1.87 ml of nitric acid at 70% in water and of 3.65 ml of sulfuric acid is added while maintaining the temperature <10° C. The reaction medium is stirred for 30 minutes at a temperature <10° C. and then stirred for one hour at ambient temperature. The reaction medium is poured into ice-cold water (250 ml). The insoluble material is filtered off under vacuum and dried, so as to give 5.2 g of 7-nitro-3,4-dihydronaphthalen-1(2H)-one in the form of a beige solid.

Workup

  1. temperaturewhile maintaining the temperature <10° C
  2. temperaturewhile maintaining the temperature <10° C
  3. stirringstirred for one hour at ambient temperature
  4. filtrationThe insoluble material is filtered off under vacuum
  5. customdried

Sources & evidence

ORD record
ord-ba73776760154ffa8916cbf1a255a5dc
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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