Bromide ion → 3-(3-Methoxyphenyl)-3-hydroxyindan-1-one

HRID 464687

Reaction equation

HRID 464687 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[Br-].[Mg].[C:13]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH2:14]1>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2([OH:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 118151,3-IndandioneHCID 5462224MagnesiumHCID 178490745HCID 178490745, compound

Product 1

HCID 202624453-(3-Methoxyphenyl)-3-hydroxyindan-1-oneYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

m-Methoxyphenyl magnesium bromide (prepared from 10 g of the corresponding bromide and 1.45 g of magnesium turnings in ether) was treated at 0° with a solution of 1,3-indandione (3.5 g) in ether. After stirring at 25° for 4.5 hours, the mixture was quenched with saturated ammonium chloride solution. The layers were separated, the aqueous layer was extracted with ether, and the organic layers were dried (MgSO4) and concentrated. Chromatography of the residue on silica gel provided the title compound as a viscous yellow oil (3.6 g, 59%). NMR and IR spectra were consistent with the assigned structure.

Workup

  1. customthe mixture was quenched with saturated ammonium chloride solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether
  4. dry with materialthe organic layers were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6cf9212a2c7d470bb5088da055a3aa98
Source dataset
uspto-grants-1985_10
Patent number
US04548946

Linked notes

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