Methanol → 7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1776975Notes

Reaction equation

HRID 1776975 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].CO.[Cl-].[NH4+]>C1COCC1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Nitro-3,4-dihydro-2H-naphthalen-1-one (2.0 g, 10 mmol) was dissolved in THF (50 mL) and NaBH4 (0.95 g, 25 mmol) was added. MeOH (50 mL) was then added dropwise over 5 minutes and the reaction mixture was stirred for one hour. Saturated ammonium chloride was then added to the reaction mixture, and the resulting mixture was extracted three times with ethyl acetate. The organic solutions were combined and washed with brine, dried (Na2SO4) and concentrated to give 7-nitro-1,2,3,4-tetrahydronaphthalen-1-ol. Yield 1.83 g (95%). LCMS (ESI): calc. C10H11NO3=193; obs. M+H=194.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8377fbc0ac254c8b8030cc99c52c91cf
Source dataset
uspto-grants-2016_02
Patent number
US09266827B2

Reaction notes

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