Sodium borohydride → 4-Phenyl-2,3-dihydro-1H-inden-2-ol

HRID 67816Notes

Reaction equation

HRID 67816 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]([OH:16])[CH2:11]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 129423874-Phenyl-2-indanone

Product 1

HCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 0.30 g (0.0014 mole) of 4-phenyl-2-indanone in 10 ml of ethanol was added portion-wise 0.03 g (0.0008 mole) of sodium borohydride. The resulting yellow colored solution was stirred at ambient temperature for 1.5 hours, then concentrated, and 50 ml of water was added. The mixture was extracted with two portions of 50 ml each of diethyl ether. The extracts were combined, dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to give, after recrystallization from hexane, 0.13 g of 4-phenyl-2-indanol. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. concentrationconcentrated
  2. addition50 ml of water was added
  3. extractionThe mixture was extracted with two portions of 50 ml each of diethyl ether
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto give
  8. customafter recrystallization from hexane, 0.13 g of 4-phenyl-2-indanol

Sources & evidence

ORD record
ord-19ca98170cb54920b8b9f84323b4bf5e
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Reaction notes

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