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

HRID 2296408Notes

Reaction equation

HRID 2296408 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:11]1[CH:13]2[CH2:14][C:15]3[C:20]([CH:12]12)=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C(OCC)C.O>[C:21]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:15]=2[CH2:14][CH:13]([OH:11])[CH2:12]3)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 132792805-Phenyl-6,6a-dihydro-1aH-indeno[1,2-b]oxireneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-olYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Under a dry argon atmosphere, a stirred solution of 9 g (0.067 mole) of aluminum chloride in 225 ml of anhydrous diethyl ether was cooled to 0° C. To this was added portionwise 9.4 g (0.245 mole) of lithium aluminum hydride. The cooling bath was removed, and the mixture stirred for 15 minutes. With the temperature being maintained at 25° C., a solution of 47.7 g (0.229 mole) of 1,2-epoxy-4-phenylindane in 175 ml of anhydrous diethyl ether was added dropwise. After complete addition, the mixture was heated at reflux for 18 hours, then cooled to 0° C. Water and an aqueous solution of sodium hydroxide were added to decompose the excess lithium aluminum hydride, and the mixture was filtered. The filter cake was washed with diethyl ether, and the filtrate and washes were combined and dried over anhydrous sodium sulfate. The mixture was filtered, and the filtrate concentrated under reduced pressure to give an oil. The oil was subjected to column chromatography on silica gel, eluting with 98:2 toluene/ethyl acetate followed by 90:10 toluene/ethyl acetate to give 31.5 g of 4-phenyl-2-indanol, mp 72°-76° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customThe cooling bath was removed
  2. additionAfter complete addition
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 18 hours
  5. temperaturecooled to 0° C
  6. filtrationthe mixture was filtered
  7. washThe filter cake was washed with diethyl ether
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe mixture was filtered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customto give an oil
  12. washeluting with 98:2 toluene/ethyl acetate

Sources & evidence

ORD record
ord-ae908d811d994dc999737b6d8db2bdc3
Source dataset
uspto-grants-1984_01
Patent number
US04429149

Reaction notes

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