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

HRID 67813Notes

Reaction equation

HRID 67813 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 mixed in water and concentrated under reduced pressure. A precipitate, which developed during concentration of the aqueous solution, was collected, 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 the reaction mixture
  4. concentrationconcentrated under reduced pressure
  5. customwas collected
  6. customdried
  7. customrecrystallized from toluene-hexane

Sources & evidence

ORD record
ord-74c248691f4e40aa9008c14db4844ed5
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Reaction notes

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