Nitric Acid → 5,6,7,8-Tetrahydro-1-nitro-2-naphthalenol

HRID 2393297Notes

Reaction equation

HRID 2393297 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].CCOCC.[N+:17]([O-])([OH:19])=[O:18]>O>[OH:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 143055,6,7,8-Tetrahydro-2-naphthol

Product 1

HCID 49137365,6,7,8-Tetrahydro-1-nitro-2-naphthalenolYield 32.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5,6,7,8-Tetrahydro-2-naphthol (50 g, 0.337 mol) was mixed with ether (400 ml), and the mixture was added dropwise with 60% nitric acid (28 ml, 0.368 mol) while the reaction temperature was kept below 15° C. , and then stirring was continued at 15° to 20° C. for 1 hour. The reaction mixture was added with water (500 ml) and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 900 g, eluent: hexane/ethyl acetate=50/1 to 60/1) to give 2-hydroxy-5,6,7,8-tetrahydro-1-nitronaphthalene (21.2 g).

Workup

  1. customwas kept below 15° C.
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography (Wako Gell C-300: 900 g, eluent: hexane/ethyl acetate=50/1 to 60/1)

Sources & evidence

ORD record
ord-e5b36d05147d4a7fa702566fb88c1532
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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