1-Indanone → 1-Indanol

HRID 2301134Notes

Reaction equation

HRID 2301134 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[CH:1]1([OH:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydride

Product 1

HCID 228191-IndanolYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Indanone (2.5 g, 19 mmol) was dissolved in ethanol (25 ml), and the solution was mixed with sodium borohydride (790 mg, 21 mmol) and stirred at room temperature for 3 hours. The reaction solution was mixed with ethyl acetate, washed with hydrochloric acid (1 N) and saturated brine and dried with anhydrous sodium sulfate, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 2.4 g (18 mmol, 93%) of the title compound.

Workup

  1. washwashed with hydrochloric acid (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography

Sources & evidence

ORD record
ord-144f611507dc436db3efec05dc2e307e
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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