Hydrochloric Acid → Indenol

HRID 2260021Notes

Reaction equation

HRID 2260021 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+].[Cl-].[Ce+3].[Cl-].[Cl-].Cl>CO.O>[CH:1]1([OH:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 118153841H-inden-1-one

Product 1

HCID 316919IndenolYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The indenone from Example 109 (0.5 g) is reduced with NaBH4 (0.05 g) and cerium chloride (0.5 g) in methanol (20 ml). The reaction in ended after 10 minutes and the reaction mixture is poured into water. The pH is taken to 5 by means of dilute HCl and the mixture is extracted with ethyl acetate. It is washed with water and the solvent is evaporated. Indenol (0.49 g; m.p. 134° C.) is obtained (yield: 99%; compound no. 110).

Workup

  1. customThe reaction
  2. extractionthe mixture is extracted with ethyl acetate
  3. washIt is washed with water
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-8715c1e83d4b4fa1bfc24d12c01a77fc
Source dataset
uspto-grants-1995_12
Patent number
US05475132

Reaction notes

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