Water → 3'-Chloro-4'-hydroxy-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 15653Notes

Reaction equation

HRID 15653 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.[Cl:18]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:18][C:3]1[C:4]([CH3:17])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)[C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 31398Chlorosuccinimide3×HCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 593425823'-Chloro-4'-hydroxy-2',6'-dimethylbiphenyl-3-carbaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (11.3 g, 50.0 mmol) in N,N-dimethylformamide (50 mL) was added N-chlorosuccinimide (6.68 g, 50.0 mmol) by small portions under ice-cooling, and the mixture was stirred at room temperature for 13 hr, and then at 50° C. for 3 hr. N-Chlorosuccinimide (1.34 g, 10.0 mmol) was added to the reaction mixture, and the mixture was stirred at the same temperature for 3 hr. N-Chlorosuccinimide (0.668 g, 5.00 mmol) was added again, and the mixture was further stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60), and the obtained crystals were recrystallized from ethyl acetate-heptane to give the title compound (8.47 g, yield 65%) as colorless crystals.

Workup

  1. temperaturecooling
  2. waitat 50° C. for 3 hr
  3. stirringthe mixture was stirred at the same temperature for 3 hr
  4. stirringthe mixture was further stirred at the same temperature for 1 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-40:60)
  10. customthe obtained crystals were recrystallized from ethyl acetate-heptane

Sources & evidence

ORD record
ord-a4dcf1f8fcc040c4884b6640190b7d6b
Source dataset
uspto-grants-2010_06
Patent number
US07732626B2

Reaction notes

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