Nitric Acid → 3-Nitro-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 325980Notes

Reaction equation

HRID 325980 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].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[N+:12]([C:3]1[C:2]([OH:11])=[CH:1][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

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

Product 1

HCID 6063293-Nitro-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5,6,7,8-tetrahydro-2-naphthol (44 g) in 300 ml of acetic acid was added dropwise fuming nitric acid (12 ml in 12 ml of acetic acid) over a period of 30 minutes. The reaction mixture was then stirred for an additional 5 hours at room temperature. After evaporation of the solvent, the crude product was purified by column chromatography (silica gel) to give 16 g of pure product, m.p. 88°-89° C.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-9c110dda3d56442f9a12f2cc993bb46f
Source dataset
uspto-grants-1984_04
Patent number
US04443610

Reaction notes

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