4-Phenyl-2,3-dihydro-1h-inden-1-one → 4-Phenyl-2,3-dihydro-1H-inden-1-ol

HRID 2296405Notes

Reaction equation

HRID 2296405 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][C:11]3=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C.O>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH:11]3[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 2633814-Phenyl-2,3-dihydro-1h-inden-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 129423854-Phenyl-2,3-dihydro-1H-inden-1-olYield 82.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 20.8 g (0.10 mole) of 4-phenyl-1-indanone in 150 ml of ethanol was added portionwise 2.0 g (0.06 mole) of sodium borohydride. During the addition the reaction temperature rose to 33° C. Upon complete addition, the reaction mixture was allowed to cool to ambient temperature and was stirred for 16 hours. The reaction mixture was diluted with water and concentrated under reduced pressure. A precipitate, which developed during concentration of the mixture, was collected and dried, then recrystallized from toluene-hexane to give 17.3 g of 4-phenyl-1-indanol; m.p. 80.5°-81.5° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionDuring the addition the reaction temperature
  2. customrose to 33° C
  3. additionUpon complete addition
  4. concentrationconcentrated under reduced pressure
  5. customwas collected
  6. customdried
  7. customrecrystallized from toluene-hexane

Sources & evidence

ORD record
ord-3d783f5c89b34d8780c29111efb9c3f4
Source dataset
uspto-grants-1984_01
Patent number
US04429149

Reaction notes

Loading…