Tetralin → 1,2,3,4-Tetrahydro-6-nitronaphthalene

HRID 1439900Notes

Reaction equation

HRID 1439900 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1>ClCCl>[N+:7]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:9][CH:10]=1)[CH2:17][CH2:16][CH2:15][CH2:14]2)([O-:8])=[O:6]

Participants

4

Reactant 2

HCID 8404TetralinHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 880181,2,3,4-Tetrahydro-6-nitronaphthaleneYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 85% nitronium tetrafluoroborate (52 g, 0.333 mol) in dichloromethane (500 mL) was added dropwise a solution of tetralin (40 g, 0.303 mol) in dichloromethane (400 mL) over 45 min at 0° C. The mixture was stirred for 30 min at 0° C. and quenched by addition of ice-water (700 mL). The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 30:1~5:1 hexane/toluene to give 14.15 g of the title compound: 1H NMR (CDCl3) δ7.91 (s, 1H), 7.88 (d, 1H, J=7.6 Hz), 7.17 (d, 1H, J=7.6 Hz), 2.84 (m, 4H), 1.83 (m, 4H).

Workup

  1. customquenched by addition of ice-water (700 mL)
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 30:1~5:1 hexane/toluene

Sources & evidence

ORD record
ord-01feedf691924b13a09568217edf85e5
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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