Water → HCID 14566727, compound

HRID 322612Notes

Reaction equation

HRID 322612 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].C1(C)C=CC=CC=1.O>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7](=[CH:6][CH:5]=1)[CH2:8][CH2:9][CH:10]=[CH:11]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 384457-Nitro-1-tetraloneHCID 4311764Sodium borohydride

Product 1

HCID 14566727HCID 14566727, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

A suspension of 7-nitrotetralone (20 g, 0.105 mol) in MeOH (300 mL) was treated with NaBH4 (4.1 g) with intermitent cooling. After the addition, cooling was removed and the reaction stirred over night. The reaction was cooled in ice-water and quenched with a solution of MeOH (200 mL) and concentrated HCl (35 mL). The solvent was evaporated, the residue was suspended in H2O, and the mixture was extracted with CHCl. The extracts were dried and the solvent evaporated to give a tan solid. A mixture of the solid, p-toluenesulfonic acid (0.4 g), and toluene (300 mL) was heated to reflux for over night with water being collected in a Dean-Stark trap. The reaction was cooled, washed with H2O, aqueous NaHCO3, and brine, then the solvent was dried and evaporated to give a dark liquid (15.6 g) that had an nmr consistent with the desired material.

Workup

  1. additionAfter the addition
  2. temperaturecooling
  3. customwas removed
  4. temperatureThe reaction was cooled in ice-water
  5. customquenched with a solution of MeOH (200 mL) and concentrated HCl (35 mL)
  6. customThe solvent was evaporated
  7. extractionthe mixture was extracted with CHCl
  8. customThe extracts were dried
  9. customthe solvent evaporated
  10. customto give a tan solid
  11. temperaturewas heated
  12. customcollected in a Dean-Stark trap
  13. temperatureThe reaction was cooled
  14. washwashed with H2O, aqueous NaHCO3, and brine
  15. customthe solvent was dried
  16. customevaporated

Sources & evidence

ORD record
ord-96a3b56c67634129a281fc0dfd3982dc
Source dataset
uspto-grants-2001_04
Patent number
US06211364B1

Reaction notes

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