Hydrochloric Acid → HCID 23031104, compound

HRID 1766647Notes

Reaction equation

HRID 1766647 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[C:17]3[C:13]=2[CH2:14][CH2:15][CH2:16]3)=[CH:7][C:4]=1[CH:5]=[O:6].B(Cl)(Cl)Cl.CO.Cl>ClCCl>[OH:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[C:17]3[C:13]=2[CH2:14][CH2:15][CH2:16]3)=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25135Boron TrichlorideHCID 230312052-Methoxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde

Product 1

HCID 23031104HCID 23031104, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Methoxy-5-(5-methyl-7-nitroindan-4-yloxy) benzaldehyde (2.03 g) was dissolved in dichloromethane (80 mL). To the solution was added dropwise a 1 mol/L solution of boron trichloride in dichloromethane (20 mL) under ice-cooling with stirring. The reaction mixture was stirred at room temperature for 24 hours. To the reaction mixture was added dropwise methanol (10 mL) under ice-cooling with stirring. After adding diluted hydrochloric acid, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (1.45 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 24 hours
  3. temperaturecooling
  4. stirringwith stirring
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-673dbc83f4e7472797f5dce0eda61ea6
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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