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

HRID 2289503Notes

Reaction equation

HRID 2289503 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-a63f9336b86849cfbfa09a44c72d833c
Source dataset
uspto-grants-2000_07
Patent number
US06093727

Reaction notes

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