Hydrochloric Acid → Indenol

HRID 1742875

Reaction equation

HRID 1742875 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 is 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. extractionthe mixture is extracted with ethyl acetate
  2. washIt is washed with water
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-cd9cf0ff7a204f888cf069744c378c51
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Linked notes

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