1-Tetralone → 7-Nitro-1-tetralone

HRID 2288062Notes

Reaction equation

HRID 2288062 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.[N+:12]([O-])([O-:14])=[O:13].[Na+]>>[N+:12]([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-:14])=[O:13]

Participants

3

Reactant 2

HCID 107241-TetraloneHCID 24268Sodium Nitrate

Product 1

HCID 384457-Nitro-1-tetraloneYield 50%

Conditions

Temperature
0 °C

Procedure

10.0 g (68 mmol) of α-tetralone were dissolved in 80 ml of conc. sulftric acid with ice-cooling. After addition of 6.4 g (75 mmol) of sodium nitrate in portions, the mixture was additionally stirred at 0° C. for 1 h and then poured onto 350 ml of ice water. The precipitated product was filtered off with suction, washed with water until neutral, dried in vacuo and recrystallized from isopropanol. 6.5 g of 7-nitro-3,4-dihydro-2H-naphthalen-1-one were obtained, m.p. 104-106° C.

Workup

  1. temperaturecooling
  2. filtrationThe precipitated product was filtered off with suction
  3. washwashed with water until neutral,
  4. customdried in vacuo
  5. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f2b453568e3f40c2847570d7a1088ca4
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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