2-Indanone → 2-Indanol

HRID 267560

Reaction equation

HRID 267560 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[BH4-].[Na+]>CO>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[OH:10]

Participants

4

Reactant 2

HCID 119832-IndanoneHCID 4311764Sodium borohydride

Product 1

HCID 779362-IndanolYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 60 g sample of 2-indanone (0.45 moles) in 1.5 liters of 40% aqueous methanol was treated with 18 g (0.46 moles) of sodium borohydride in portions with cooling to maintain T≤ 40°C. After the addition was complete (15 min), the mixture was stirred for 2 hrs then allowed to stand overnight at room temp. Ether extraction, drying over potassium carbonate and evaporation gave 58.3 g crystalline 2-indanol (96%).

Workup

  1. temperaturewith cooling
  2. additionAfter the addition
  3. custom(15 min)
  4. waitto stand overnight at room temp
  5. extractionEther extraction
  6. dry with materialdrying over potassium carbonate and evaporation

Sources & evidence

ORD record
ord-6c8acacc781249eebb82cb28dffc8a49
Source dataset
uspto-grants-1976_03
Patent number
US03943149

Linked notes

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