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

HRID 1836277Notes

Reaction equation

HRID 1836277 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-a4978449b4d5483d86f78bc64c7105dd
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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