1,3-Indandione → 3-Hydroxy-2,3-dihydro-1H-inden-1-one

HRID 1679082Notes

Reaction equation

HRID 1679082 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1.[H][H].[BH4-].[Na+]>[Pd]>[OH:11][CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1

Participants

5

Reactant 3

HCID 118151,3-IndandioneHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 1764483-Hydroxy-2,3-dihydro-1H-inden-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 73.25 g. (0.5 mole) of 1,3-indandione, 10.0 g. of 10% Pd on charcoal and 800 ml. of 2B-ethanol was added on the 1 liter flask of a Brown Hydrogenator, and hydrogen equivalent to 125 ml. of 1M sodium borohydride solution was added at room temperature and atmospheric pressure (0.5 mole H2). The solution was filtered through a bed of Celite Filter Aid, and the bed washed with ethanol. The ethanol solution was concentrated, and from the concentrate, a small amount of white solid separated, 1,3-indanediol, 1,6 g., m.p. 182°-187°. This by-product was filtered off and discarded. Evaporation of the filtrate gave 70.2 g. of nearly colorless oil (yield > 95%) which can be used directly in the aldehyde condensation. The IR spectrum of the product showed typical hydroxyl and carbonyl absorption.

Workup

  1. additionA mixture of 73.25 g
  2. filtrationThe solution was filtered through a bed of Celite
  3. filtrationFilter Aid
  4. washthe bed washed with ethanol
  5. concentrationThe ethanol solution was concentrated
  6. customfrom the concentrate, a small amount of white solid separated
  7. filtrationThis by-product was filtered off
  8. customEvaporation of the filtrate
  9. customgave 70.2 g

Sources & evidence

ORD record
ord-00dd33ff56c341d5a76ca08145ac81ca
Source dataset
uspto-grants-1978_03
Patent number
US04078934

Reaction notes

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