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

HRID 1756779Notes

Reaction equation

HRID 1756779 reaction equation
[C:1]1(O)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13].CC[O:18]CC>>[N+:12]([C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:18])([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 49137365,6,7,8-Tetrahydro-1-nitro-2-naphthalenol

Procedure

To a solution of 25.9 g of 5, 6, 7, 8-tetrahydronaphthol in 210 ml of ether was dropwise added 60% nitric acid at 15°-20° C. with stirring in 1 hour, and the resultant mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water (6 times) and saturated saline and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (1:15) to give 10.12 g of 1-nitro-5, 6, 7, 8-tetrahydro-2-naphthol.

Workup

  1. customat 15°-20° C.
  2. washThe reaction mixture was washed with water (6 times) and saturated saline
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel
  6. washeluting with ethyl acetate/n-hexane (1:15)

Sources & evidence

ORD record
ord-5f361afd91c644e883cf16e3cd607238
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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