Water → 1-Indanol

HRID 1646606Notes

Reaction equation

HRID 1646606 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+].O.[Cl-].[Na+]>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

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 67351-IndanoneHCID 4311764Sodium borohydride2×

Product 1

HCID 228191-IndanolYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.28 g of 1-indanone in 13 ml of anhydrous ethanol is cooled to +5° C. 0.23 g of sodium borohydride at 95% is added in small fractions, with agitation at +10° C. for one hour. 0.23 g of sodium borohydride at 95% is again added at +5° C., with agitation at 20° C. for one hour 30 minutes. The reaction mixture is poured into 60 ml of water containing sodium chloride and is extracted with isopropyl ether; the extracts are dried and brought to dryness under reduced pressure and the residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4). 1.15 g of expected product is isolated.

Workup

  1. extractionis extracted with isopropyl ether
  2. customthe extracts are dried
  3. customthe residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4)

Sources & evidence

ORD record
ord-d9da3b9a055c464da707adf5c3b556d5
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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