Water → 7-methoxy-2,3-dihydro-1H-inden-4-ol

HRID 1099348Notes

Reaction equation

HRID 1099348 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2.B(Br)(Br)Br.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8]=2[C:9]([OH:12])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 126541332,3-Dihydro-4,7-dimethoxy-1H-indene

Product 1

HCID 206091567-methoxy-2,3-dihydro-1H-inden-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To the clear solution of 4,7-Dimethoxyindane (22.5 gm, 0.126 mole) in Methylene chloride (400 ml), added Boron tribromide (12.27 ml, 0.13 mole) at 0° C. After 2 hours stirring at 0-10° C., water (100 ml) was added and then the reaction mixture was extracted with Methylene chloride. The Methylene chloride layer was dried over Sodium sulphate and distilled off to give a crude mass which was purified by column chromatography using 7% Ethyl acetate in Hexane (9.0 gm).

Workup

  1. extractionthe reaction mixture was extracted with Methylene chloride
  2. dry with materialThe Methylene chloride layer was dried over Sodium sulphate
  3. distillationdistilled off
  4. customto give a crude mass which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-020430c6802a42c9a2b72061b0ffdf76
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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