Hydrochloric Acid → HCID 23031138, compound

HRID 1766648Notes

Reaction equation

HRID 1766648 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[C:16]3[C:12]=2[CH2:13][CH2:14][CH2:15]3)=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>CN(C)C=O>[CH2:30]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[C:16]3[C:12]=2[CH2:13][CH2:14][CH2:15]3)=[CH:6][C:3]=1[CH:4]=[O:5])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23031104HCID 23031104, compound

Product 1

HCID 23031138HCID 23031138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-hydroxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde (3.20 g) and potassium carbonate (1.55 g) in N,N-dimethylformamide (25 mL) was stirred under ice-cooling. After adding dropwise benzyl bromide (1.34 mL), the mixture was stirred at room temperature for 24 hours. The reaction mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (3.30 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-12fb6cc5c3d644f790285ff4767123ec
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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