Hydrochloric Acid → 4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde

HRID 493478Notes

Reaction equation

HRID 493478 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#N)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.Cl.[OH2:28]>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 93892[1,1'-Biphenyl]-4-carbonitrile, 4'-methoxy-HCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Diisobutyl-aluminum hydride (86 mL of a 1 M solution in methylene chloride, 86 mmol) was added under nitrogen dropwise over 1 h to a solution of 4′-methoxy-1,1′-biphenyl-4-carbonitrile (15.0 g, 71.7 mmol), prepared in the previous step, in 500 mL of methylene chloride at ice bath temperature. After the addition the ice bath was removed and the reaction was stirred at room temperature for 1 h. By TLC starting material remained. The reaction was cooled to ice bath temperature and an additional 60 mL (60 mmol) of the diisobutylaluminum hydride was added dropwise over 1 h. After the addition the reaction was stirred at room temperature for 16 h. At room temperature 2 N HCl was added slowly until the reaction was acidic. Additional water and methylene chloride were added and the mixture filtered. The organic layer was then separated and the aqueous layer extracted multiple times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 4′-methoxy-1,1′-biphenyl-4-carbaldehyde (12.5 g, 82%) as a pale yellow solid, MS (EI) m/z 212. Elemental Analysis for C14H12O2. Calc'd: C, 79.23; H, 5.70; N, 0.00. Found: C, 77.92; H, 5.87; N, 0.00

Workup

  1. customwas removed
  2. temperatureThe reaction was cooled to ice bath temperature
  3. additionAfter the addition the reaction
  4. stirringwas stirred at room temperature for 16 h
  5. filtrationthe mixture filtered
  6. customThe organic layer was then separated
  7. extractionthe aqueous layer extracted multiple times with methylene chloride
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c8d5fabc8ad84b16aca56e0e402defce
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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