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

HRID 1597344Notes

Reaction equation

HRID 1597344 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+]>CCO>[OH:14][CH:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7-nitro-1-tetralone (2.00 g, 10.5 mmol) in EtOH (15 mL) was cooled by an ice water bath and treated with NaBH4 (0.40 g, 10.6 mmol). The mixture was stirred at room temperature for 2 h and then poured into ice water (50 mL) and extracted with EtOAc (3×20 mL). The extract was washed with NaCl solution, dried (MgSO4), filtered and concentrated to give a white solid (1.92 g, 95% yield).

Workup

  1. temperaturewas cooled by an ice water bath
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe extract was washed with NaCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-489c862faf5d4e7a8b1510ee61b1ca1a
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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